MN15: A New Kohn-Sham Density Functional with Broad ... · 0 2006 b97-d 21 0 2009 mohlyp2 22 0 2009 orelyp 10,18,23 nga nga 0 2012 n12 24 0 2015 gam 25 meta-gga mgga 0 1998 vsxc 26

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ELECTRONICSUPPORTINGINFORMATION

forapaperinChemicalScienceentitled

MN15: A New Kohn-Sham Density Functional with Broad Accuracy for Multi-reference and Single-reference

Systems and Noncovalent Interactions

HaoyuS.Yu,aXiaoHe,a,b,cShaohongL.Li, aandDonaldG.Truhlar*aaDepartment of Chemistry, Chemical Theory Center, Inorganometallic Catalyst Design Center, and Supercomputing Institute, University of Minnesota, Minneapolis, Minnesota 55455-0431, USA. *E-mail: [email protected] Key Laboratory of Precision Spectroscopy and Department of Physics, East China Normal University, Shanghai, 200062, China cNYU-ECNU Center for Computational Chemistry at NYU Shanghai, Shanghai, 200062, China

March 31, 2016

Tableofcontents

Density functionals tested in this paper and SI. S-3 Grids, basis sets, and geometries S-4 Table S1. 83 density functionals tested in the paper and SI with the

percentage of nonlocal Hartree-Fock exchange, the year that the functional was published, and the original reference or references S-5

Table S2. The mean unsigned errors on 27 databases of atomic and

molecular energies as calculated by local spin density approximations (LSDAs) and generalized gradient approximations (GGAs) S-8

Table S3. The mean unsigned errors on 27 databases of atomic and molecular energies as calculated by GGAs, N12, GAM, and

global hybrid GGAs S-9 Table S4. The mean unsigned errors on 27 databases of atomic and

molecular energies as calculated by range-separated hybrid GGAs and global hybrid GGAs S-10

Electronic Supplementary Material (ESI) for Chemical Science.This journal is © The Royal Society of Chemistry 2016

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Table S5. The mean unsigned errors on 27 databases of atomic and molecular energies as calculated by range-separated hybrid GGAs, N12-SX, meta-GGAs, and MN15-L S-11

Table S6. The mean unsigned errors on 27 databases of atomic and

molecular energies as calculated by hybrid meta-GGAs S-12 Table S7. The mean unsigned errors on 27 databases of atomic and

molecular energies as calculated by hybrid meta-GGAs, M11, MN12-SX, and MN15 S-13 Table S8. The mean unsigned errors intermolecular charge transfer database (CT7)

calculated by 83 density functionals in the order of increasing MUE of CT7 database S-14 Table S9. The mean unsigned errors for molecular energy database and its subdatabases calculated by 83 density functionals in the same order as Table S1 S-15 Table S10. The average and median mean unsigned errors for the molecular

energy database and its subdatabases calculated by 83 density functionals S-17

Table S11. The mean unsigned errors for molecular energy databases and its subdatabases calculated by 83 density functionals in the order of increasing MUE of atomic and molecular database (AME471) S-18 Table S12. The mean unsigned errors on three molecular databases calculated by 83 density functionals in the same order as Table S1 S-20 Table S13. The mean unsigned errors on three molecular databases calculated by 83 density functionals in the order of increasing MUE of

molecular structure database (MS10) S-21 Table S14. Geometries, charge, and multiplicities of alkyl bond dissociation

energies (ABDE13), six dimers at six intermonomer distances (S6x6), semiconductor band gaps (SBG31), and excitation energies of selected organic molecules (EE69) S-22

References S-65

S-3

Density functionals tested in the paper and supporting information In order to evaluate the performance of the MN15 functional, we tested a large number of previously developed density functionals for comparison; In particular, we tested 82 previously developed density functionals of 12 types plus the present MN15 functional, which is a 13th type. The full set of functionals tested, sorted by type and by year within a type, is as follows:

• LSDA: GKSVWN5,1,2,3 GKSVWN3, 1,2,3

• GGA: SOGGA,4 PBEsol,5 SOGGA11,6 B86P86,7,8 B86LYP,7,10 BP86,8,9 BLYP,9,10 BR89LYP,10,11 B86PW91,7,12 PW91,12 BPW91,9,12 PBE,13

mPWPW,14 revPBE,15 RPBE,16 HCTH407,17 OLYP,10,18 MPWLYP1W,19

PBE1W,19 PBELYP1W,19 MOHLYP,20 B97-D,21 MOHLYP2,22 and

OreLYP10,18,23

• NGA: N1224 and GAM25

• meta-GGA: VSXC,26 τ-HCTC,27 TPSS,28 TPSSLYP1W,19 M06-L,29 revTPSS,30 M11-L,31 MGGA_MS232

• meta-NGA: MN12-L33 and MN15-L34

• global hybrid GGA: HFLYP,10,35 HFPW91,12, 35 B3PW91,9,36 B3LYP,9,10,37 PBE0,38 mPW1PW,39 B1LYP,40 B98,41 B97-1,42 MPW1K,43 O3LYP,44

B97-2,45 MPW3LYP,46 MPWLYP1M,20 B97-3,47 and SOGGA11-X48

• range-separated hybrid-GGA: CAM-B3LYP,49 LC-ωPBE,50, 51,52,53, HSE06,54,55 ωB97,56 ωB97X56

• range-separated hybrid-GGA plus molecular mechanics (also called empirical dispersion correction): ωB97X-D57

• range-separated-hybrid-NGA: N12-SX58

• global hybrid meta-GGA: TPSSh,59 τ-HCTHhyb,27 BB1K,9,60,61 MPWB1K,46 MPW1B95,46 BMK,62 TPSS1KCIS,63 MPWKCIS1K,22

MPW1KCIS,22 PBE1KCIS,64 PWB6K,65 PW6B95,65 M05,66 M05-2X,67

M06-HF,68 M06,69 M06-2X,69 M08-HX,70 M08-SO70

• range-separated-hybrid meta-GGA: M11 71

• range-separated-hybrid meta-NGA: MN12-SX58

• global-hybrid meta-NGA: MN15

S-4

For each of the functionals in the above list, Table S1 shows the percentage of nonlocal Hartree-Fock exchange, the year that the functional was published, and the original reference or references.

S-5

Grids, basis sets, and geometries

An ultrafine grid (99 radial shells with 590 angular points per shell) is used for

integration of density functionals.

The Gaussian 09 keyword stable=opt is used for finding the lowest-energy

solution to the Kohn-Sham equations by breaking the symmetry of the Slater

determinant when necessary.

The basis sets and geometries used for molecules that are also in a previous

database called Database 2015A are the same as specified previously.34 The def2-

QZVP basis set72 is used for the 36 weak interactions and S66x8 database. The ma-

TZVP basis set73 is used for the 13 alkyl bond dissociation energies. The 6-311(2+,

2+)G** basis set as proposed by Wiberg et al.74 is used for calculations of excitation

energies of selected organic molecules. For the transition metal barrier height test sets,

the cc-pVQZ75 basis set is used for H, B, C, N, and O; the cc-pV(Q+d)Z76 basis set is

used for P, S, and Cl; the cc-pVQZ-PP77,78 basis set is for Mo, W, and Zr; the cc-

pVTZ,75 cc-pV(T+d)Z,76 and cc-pVTZ-PP78 basis sets are used for reactions that

involves Re atoms. The aug-cc-pVTZ75,79 basis set is used for testing the geometries

of 47 organic molecules (SE47).

The geometries that are used for transition metal barrier heights database

(TMBH21) are reported in the supporting information of the original papers.80,81,82

The reference geometries for the SE47 test set are reported in reference 83. The

geometries used for calculating semiconductor band gaps (database SBG31), alkyl

bond dissociation energies (ABDE13), six dimers at six intermonomer distances

(S6x6 ), and excitation energies of selected organic molecules (EE69) are reported in

this supporting information.

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Table S1. Exchange–correlation functionals tested in this study

Category Type Abbrev. X a Year Method Ref.

local LSDA LSDA 0 1980 GKSVWN5b 1,2,3 0 1980 GKSVWN3b 1,2,3

GGA - exchange correct GGA 0 2008 SOGGA 4 to second order 0 2008 PBEsol 5 0 2011 SOGGA11 6 GGA - other GGA 0 1986 B86P86 7,8 0 1987 B86LYP 7,10 0 1988 BP86 8,9 0 1988 BLYP 9,10 0 1989 BR89LYP 10,11 0 1991 B86PW91 7,12 0 1991 PW91c 12 0 1991 BPW91 9,12 0 1996 PBE 13 0 1997 mPWPW 14 0 1997 revPBE 15 0 1999 RPBE 16 0 2001 HCTH407 17 0 2001 OLYP 10,18 0 2005 MPWLYP1

W 19

0 2005 PBE1W 19 0 2005 PBELYP1W 19 0 2005 MOHLYP 20 0 2006 B97-D 21 0 2009 MOHLYP2 22 0 2009 OreLYP 10,18,23 NGA NGA 0 2012 N12 24 0 2015 GAM 25 meta-GGA mGGA 0 1998 VSXC 26 0 2002 τ-HCTH 27 0 2003 TPSS 28 0 2005 TPSSLYP1

W 19

0 2006 M06-L 29 0 2009 revTPSS 30 0 2011 M11-L 31 0 2013 MGGA_MS2 32 meta-NGA mNGA 0 2012 MN12-L 33 0 2015 MN15-L 34 nonlocal global-hybrid GGA GGAh 100 1987 HFLYP 10,35 100 1991 HFPW91 12,35 20 1992 B3PW91 9,36 20 1994 B3LYP 9,10,37 25 1996 PBE0 38 25 1997 mPW1PW 39

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25 1997 B1LYP 40 21.98 1998 B98 41 21 1998 B97-1 42 42.80 2000 MPW1K 43 11.61 2001 O3LYP 44 21 2001 B97-2 45 21.8 2004 MPW3LYP 46 5 2005 MPWLYP1

M 20

26.93 2005 B97-3 47 35.42 2011 SOGGA11-X 48 RS-hybrid GGAd GGArsh 19-65 2004 CAM-

B3LYP 49

0-100 2006 LC-ωPBE 50-53 25-0 2006 HSE06 54,55 0-100 2008 ωB97 56 15.77-100 2008 ωB97X 56 RS-hybrid NGA NGArsh 25-0 2012 N12-SX 58 RS-hybrid GGA+MMe NGArsh-D 22.2-100 2008 ωB97X-D 57 global-hybrid meta-GGA mGGAh 10 2002 TPSSh 59 15 2002 τ-HCTHhyb 27 42 2004 BB1K 9,60,61 44 2004 MPWB1K 46 31 2004 MPW1B95 46 42 2004 BMK 62 13 2005 TPSS1KCIS 63 41 2005 MPWKCIS1

K 22

15 2005 MPW1KCIS 22 22 2005 PBE1KCIS 64 46 2005 PWB6K 65 28 2005 PW6B95 65

28 2005 M05 66

56 2005 M05-2X 67

100 2006 M06-HF 68

27 2008 M06 69 54 2008 M06-2X 69 52.23 2008 M08-HX 70 56.79 2008 M08-SO 70 RS-hybrid meta-GGAd

GGA mGGArsh 42.8-100 2011 M11 71

RS-hybrid meta-NGA mNGArsh 25-0 2012 MN12-SX 58 global-hybrid meta-NGA mNGAh 44 2015 MN15 present

a X is the percentage of nonlocal Hartree–Fock exchange. When a range is given, the first value is for small interelectronic distances, and the second value is for large interelectronic distances. Details of the functional form that joins these regions of interelectronic separation are given in the references.

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b GVWN5 denotes the Gáspár approximation for exchange and the VWN5 fit to the correlation energy; GVWN3 denotes Gáspár approximation for exchange and the VWN fit to the correlation energy; this is an example of the local spin density approximation (LSDA), and it has the keyword SVWN5 and SVWN in the Gaussian 09 program. Note that Kohn-Sham exchange is the same as Gáspár exchange, but Slater exchange (not tested here) is greater by a factor of 1.5.

c PW91 formally satisfies the gradient expansion for exchange to second order but only at such small values of the gradient that for practical purposes it should be grouped with functionals that do not satisfy the gradient expansion to second order.

d RS denotes range-separated.

e MM denotes molecular mechanics (also called empirical dispersion correction), which in this case corresponds to atom-atom pairwise damped dispersion terms added post-SCF to the calculated energy.

S-9

Table S2. MUEs (kcal/mol) for the AME471 database and subdatabases: LSDA, GGA

Type ——LSDA—— ————————————————————————— GGA—————————————————————————

Functional SVWN5 SVWN3 B86P86 B86LYP BP86 BLYP BR89LYP B86PW91 BPW91 PW91 PBE HCTH407 mPWPW revPBE RPBE OLYP MPWLYP1W SR-MGM-BE9 12.54 14.77 3.58 4.46 3.28 5.50 4.95 2.65 3.52 2.62 2.72 3.87 3.07 4.72 5.06 5.14 5.05

SR-MGN-BE107 16.21 17.88 3.94 2.87 4.06 2.78 2.72 2.51 2.49 3.51 3.40 2.55 2.80 2.99 3.35 2.32 2.60 SR-TM-BE17 20.34 22.71 6.46 6.40 6.84 6.20 5.90 5.60 6.79 8.22 7.20 8.05 6.18 5.67 5.76 9.01 8.03

MR-MGM-BE4 24.56 27.63 9.94 7.64 9.49 8.75 8.65 7.55 8.03 10.26 9.31 10.11 9.02 6.24 6.43 8.39 10.57 MR-MGN-BE17 36.89 40.23 6.59 8.20 13.87 6.67 5.79 12.15 10.74 14.80 14.80 5.24 12.45 5.94 5.51 5.15 10.88 MR-TM-BE13 26.60 29.02 22.93 20.62 9.68 9.80 6.48 7.85 8.82 10.18 12.73 19.53 9.22 7.39 6.80 5.58 11.93

IsoL6/11 2.05 2.19 1.35 2.63 2.28 3.73 3.59 1.34 2.38 1.92 1.98 3.02 2.16 2.82 2.99 3.44 3.67 IP23 9.59 19.89 8.97 5.84 8.44 6.52 8.68 6.69 6.30 7.29 6.19 6.81 6.85 5.00 4.92 3.12 7.16

EA13/03 5.70 16.41 2.57 4.18 4.21 2.68 5.50 3.98 2.26 2.60 2.27 3.70 2.31 2.40 2.37 3.60 3.20 PA8 5.07 4.55 3.59 2.68 1.41 1.58 4.28 4.89 1.88 1.30 1.34 2.84 1.52 2.00 1.98 2.40 1.61 πTC13 4.80 4.66 10.36 10.24 5.85 6.07 4.39 11.65 7.08 5.73 5.59 8.23 6.41 7.15 7.20 8.26 5.96

HTBH38/08 17.56 17.79 7.74 6.21 9.16 7.52 5.56 5.93 7.38 9.60 9.31 5.48 8.43 6.58 6.43 5.63 8.17 NHTBH38/08 12.42 12.36 7.97 7.83 8.72 8.53 8.08 6.53 7.26 8.80 8.42 6.29 8.03 6.82 6.82 5.25 9.04

NCCE30 3.29 3.44 2.54 2.50 1.73 1.84 1.57 2.48 2.02 1.48 1.42 1.28 1.51 1.90 1.72 2.81 1.50 AE17 421.13 309.99 29.64 24.85 16.92 8.68 28.42 24.67 11.95 4.63 47.24 16.80 12.55 10.88 9.39 10.13 35.60

HC7/11 21.45 23.50 6.33 19.48 9.95 27.39 31.82 5.02 10.77 4.55 3.97 14.97 8.08 13.65 14.96 17.01 26.30 3dEE8 12.79 14.04 10.58 12.82 11.14 11.92 9.77 10.82 13.84 11.12 11.88 14.53 11.22 10.56 10.31 12.00 12.08

4dAEE5 14.10 5.28 9.57 6.30 5.07 5.73 7.69 4.70 5.03 4.73 4.70 7.75 4.89 4.49 4.27 5.94 5.67 pEE5 4.36 5.56 3.11 8.20 3.46 5.10 8.14 3.62 6.33 4.14 3.96 4.27 5.22 4.37 3.51 2.09 6.24

DC9/12 17.35 20.43 5.78 7.32 15.11 17.88 12.20 6.60 16.21 13.94 14.99 19.74 14.76 20.35 21.48 21.71 16.24 2pIsoE4 2.05 2.05 3.38 5.57 3.21 5.45 6.23 3.63 3.43 2.87 2.73 4.59 3.20 3.59 3.70 3.95 5.47 4pIsoE4 3.05 2.97 3.01 4.20 2.87 4.00 5.25 2.56 2.41 2.58 2.43 3.29 2.50 2.16 2.16 2.15 4.03

NGDWI21 0.21 0.23 0.08 0.18 0.53 0.38 0.16 0.14 0.59 0.16 0.10 0.25 0.22 0.28 0.18 0.32 0.18 MR-TMD-BE3 46.72 51.26 162.16 153.88 18.80 30.80 10.56 15.80 24.36 22.17 23.71 16.16 22.10 19.94 18.68 17.38 13.11

SMAE3 99.54 109.72 13.93 8.17 16.39 6.39 9.84 5.46 4.58 17.49 17.50 7.45 13.66 7.89 11.17 5.16 4.80 S6x6 3.12 3.38 2.66 3.58 4.13 4.96 3.33 3.92 5.39 2.28 2.66 4.61 3.81 5.60 5.30 7.90 3.78

ABDE13 13.96 16.10 7.26 11.96 7.35 11.98 11.28 9.21 9.32 4.96 5.08 10.17 7.37 11.43 12.02 11.25 10.82

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Table S3. MUEs (kcal/mol) for the AME471 database and subdatabases: GGA, NGA, GGAh

Type —————————————————GGA————————————————— —-NGA— ————————GGAh————————

Functional PBE1W PBELYP1W

MOHLYP B97-D SOGGA PBEsol MOHLYP2 SOGGA11 OreLYP N12 GAM HFLYP HFPW91 B3PW91 B3LYP PBE0 SR-MGM-BE9 3.51 5.43 8.21 6.56 4.73 4.74 22.29 9.00 4.44 6.06 2.00 11.00 13.99 3.83 4.58 3.65

SR-MGN-BE107 3.05 2.99 3.96 2.13 7.27 7.28 19.76 2.77 2.56 2.38 2.27 9.68 14.71 2.03 2.45 1.98 SR-TM-BE17 7.79 7.54 8.78 17.85 11.04 10.78 16.80 10.89 7.15 7.76 6.31 16.15 15.43 5.03 5.48 4.35

MR-MGM-BE4 10.47 10.60 75.40 11.30 14.48 15.81 12.63 7.44 8.35 9.10 7.76 40.94 42.75 9.10 7.76 8.94 MR-MGN-BE17 12.86 10.97 4.89 3.78 21.29 23.16 28.58 8.57 4.25 6.93 4.22 48.43 189.76 4.82 5.09 5.15 MR-TM-BE13 8.81 7.60 7.80 7.29 16.78 16.28 19.07 16.57 4.92 9.39 4.94 30.93 28.85 4.96 5.33 4.47

IsoL6/11 2.42 3.95 4.31 1.73 1.89 1.55 6.80 1.73 3.39 1.73 1.96 3.21 4.30 1.52 2.61 1.38 IP23 7.89 9.13 3.84 3.09 4.84 5.82 10.15 5.92 3.03 4.36 4.53 9.47 24.71 4.81 5.51 3.39

EA13/03 3.67 5.39 3.67 2.46 2.70 2.16 13.20 5.23 2.32 4.12 4.49 9.52 10.47 2.13 2.33 2.79 PA8 1.44 1.65 1.86 3.15 2.33 2.10 5.28 2.11 1.70 1.35 3.84 3.32 8.41 1.89 1.02 1.19 πTC13 6.14 6.28 6.67 8.82 4.06 4.20 10.81 7.41 7.27 8.61 8.59 9.65 16.74 7.00 6.03 6.11

HTBH38/08 8.45 7.85 5.49 7.17 12.88 12.69 4.14 6.57 6.28 6.94 5.35 7.22 14.98 4.03 4.23 4.22 NHTBH38/08 8.20 8.79 5.80 6.34 9.68 9.86 3.41 4.32 5.57 6.86 5.15 7.04 9.53 3.62 4.55 3.43

NCCE30 1.38 1.39 3.36 0.67 1.98 1.95 6.21 1.30 3.00 1.62 1.29 0.75 40.42 1.43 1.19 0.85 AE17 9.26 63.05 256.11 10.33 283.06 245.90 14.80 10.06 2.37 14.21 10.18 8.53 10.25 4.83 18.29 38.57

HC7/11 12.25 28.09 25.50 13.46 17.88 13.31 47.73 6.26 16.34 4.27 6.24 16.49 25.72 4.35 16.80 9.40 3dEE8 11.16 12.35 10.51 15.87 11.26 11.31 9.79 13.78 12.37 20.80 10.45 13.37 17.79 9.42 9.46 8.90

4dAEE5 4.65 5.74 5.36 10.01 4.77 8.48 3.17 7.60 6.42 10.24 5.23 6.78 5.04 4.79 5.67 4.69 pEE5 3.46 7.29 4.18 9.40 6.30 5.15 14.21 5.01 3.25 14.86 2.99 4.15 11.87 5.57 2.87 5.74

DC9/12 15.73 17.41 29.07 16.45 14.61 13.34 54.06 16.65 22.57 10.20 23.07 17.08 22.27 10.95 12.02 8.81 2pIsoE4 3.69 5.63 4.33 4.07 1.44 1.71 6.53 1.72 3.72 3.41 5.02 3.45 1.95 2.88 4.69 2.17 4pIsoE4 2.83 4.14 2.73 3.60 2.29 2.28 4.99 3.27 2.22 1.73 3.57 5.46 3.21 2.67 4.24 2.32

NGDWI21 0.11 0.15 0.41 0.07 0.08 0.08 0.41 0.65 0.39 0.39 0.02 0.09 0.19 0.45 0.28 0.11 MR-TMD-BE3 19.11 12.59 28.02 21.64 29.78 27.86 46.53 20.50 9.48 18.30 11.53 204.96 261.62 52.71 26.41 67.94

SMAE3 9.70 4.07 17.20 11.00 50.60 49.03 100.51 18.63 5.29 7.76 5.54 79.36 71.69 9.24 13.24 8.38 S6x6 3.56 2.61 9.11 0.52 2.19 2.26 14.39 4.06 8.23 3.97 1.68 2.63 2.39 4.26 3.78 2.44

ABDE13 7.53 11.03 15.23 9.21 4.21 3.25 33.05 3.75 10.77 3.84 6.28 7.39 5.36 7.00 8.65 4.27

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Table S4. MUEs (kcal/mol) for AME471 and subdatabases: GGAh, GGArsh

Type ——————————————————————GGAh—————————————————————— —————GGArsh—————

Functional mPW1PW B1LYP B98 B97-1 MPW1K O3LYP MPW3LYP MPWLYP1M B97-2 B97-3 SOGGA11-X CAM-B3LYP LC-ωPBE HSE

SR-MGM-BE9 4.09 6.44 2.42 2.17 6.06 5.18 5.72 4.86 2.09 3.08 4.27 4.04 3.28 3.77 SR-MGN-BE107 2.44 4.17 1.67 1.51 3.99 2.25 2.03 2.35 1.55 1.70 1.67 1.92 2.31 2.08

SR-TM-BE17 4.57 6.64 3.34 4.17 8.12 11.01 6.02 5.79 4.19 3.91 6.24 6.27 8.02 4.41 MR-MGM-BE4 8.64 8.55 6.60 6.05 11.00 8.31 21.77 8.84 6.63 6.96 10.50 10.45 14.00 8.52 MR-MGN-BE17 6.58 8.97 4.91 3.22 16.81 4.92 4.99 6.76 3.57 5.07 7.12 6.80 8.20 5.30 MR-TM-BE13 5.31 7.30 2.60 2.87 11.30 4.63 3.56 5.82 2.65 5.08 8.31 4.11 3.71 4.56

IsoL6/11 1.44 2.70 1.93 1.82 1.75 2.82 2.34 3.30 1.83 2.07 1.85 2.07 1.90 1.25 IP23 4.11 3.45 3.33 2.61 3.64 3.64 4.97 6.07 2.99 3.31 4.11 4.91 6.40 4.06

EA13/03 2.68 3.69 1.90 2.08 3.71 2.97 2.20 2.62 2.94 2.13 1.55 2.06 2.15 2.77 PA8 1.77 1.06 1.53 1.57 2.41 2.36 0.97 1.47 3.15 2.54 1.85 1.41 1.83 1.10 πTC13 6.85 6.03 7.13 7.04 7.28 8.00 5.46 5.60 8.16 7.37 6.08 3.69 4.27 6.20

HTBH38/08 3.55 3.19 4.16 4.39 1.34 4.06 4.71 7.48 3.24 2.28 1.79 3.18 1.18 4.23 NHTBH38/08 5.71 3.63 3.31 3.38 1.72 3.64 4.86 8.18 2.19 1.38 1.16 2.61 2.36 3.73

NCCE30 0.95 1.22 0.87 0.85 0.79 2.29 0.98 1.36 1.25 1.19 0.81 0.80 0.97 0.91 AE17 10.78 9.88 4.91 5.47 9.93 5.57 5.19 12.09 10.56 6.80 4.98 10.93 25.34 32.82

HC7/11 6.70 17.64 8.46 6.25 12.98 12.52 14.00 22.96 6.18 7.58 7.27 6.21 17.66 7.34 3dEE8 9.68 11.60 10.35 10.49 10.98 9.20 12.29 11.16 10.66 7.71 6.68 8.63 10.60 11.48

4dAEE5 4.81 5.89 6.84 7.27 4.73 5.46 5.63 5.70 8.06 6.96 4.34 5.67 5.72 5.07 pEE5 6.03 2.99 2.38 2.25 7.32 1.55 3.65 5.89 2.99 3.03 3.49 2.84 7.79 5.70

DC9/12 9.43 13.72 9.19 9.79 7.27 17.46 9.83 14.69 11.86 11.08 7.46 5.33 6.08 9.08 2pIsoE4 2.42 4.80 3.23 2.90 2.32 3.63 4.49 5.18 3.18 3.10 2.00 3.16 1.14 2.44 4pIsoE4 2.52 4.52 2.80 2.51 2.76 2.56 4.27 4.10 2.97 2.76 3.01 3.86 1.44 2.64

NGDWI21 0.21 0.28 0.10 0.08 0.20 0.27 0.15 0.17 0.24 0.40 0.43 0.15 0.23 0.10 MR-TMD-BE3 64.47 73.68 45.89 21.79 112.93 32.96 58.38 10.93 22.00 64.14 96.53 64.89 75.23 64.36

SMAE3 13.69 27.14 7.93 4.18 29.09 9.01 11.95 4.83 5.89 7.47 11.35 10.31 8.48 10.53

S6x6 3.22 3.89 2.87 2.45 2.85 6.67 2.58 3.28 4.19 3.85 2.70 2.52 2.83 2.36

ABDE13 6.09 10.04 7.41 4.00 5.30 9.36 7.08 9.76 3.78 3.92 0.98 4.94 3.67 4.94

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Table S5. MUEs (kcal/mol) for the AME471 database and subdatabases: GGArsh, NGArsh, mGGA, mNGA

Type —GGArsh— GGArsh-D NGArsh ——-———————————————mGGA———————-—————————— mNGA

Functional ωB97 ωB97X ωB97X-D N12-SX VSXC τ-HCTH TPSS TPSSLYP1W M06-L revTPSS M11-L MN12-L MGGA_MS2 MN15-L SR-MGM-BE9 3.39 3.09 2.60 1.63 2.20 3.22 2.55 4.54 3.40 3.29 7.50 3.07 6.26 2.77

SR-MGN-BE107 1.52 1.43 1.37 1.55 2.06 2.15 2.43 4.05 2.03 2.24 1.75 1.37 2.62 1.39

SR-TM-BE17 6.91 6.30 3.74 5.89 6.78 8.98 6.11 7.17 6.24 5.97 5.66 8.64 6.63 3.65 MR-MGM-BE4 8.31 11.86 9.49 8.27 7.74 10.73 6.69 8.53 6.15 5.99 13.56 19.21 8.48 1.88 MR-MGN-BE17 7.74 7.11 6.33 6.09 3.79 4.77 4.25 4.79 3.11 4.61 4.05 4.27 7.86 2.08 MR-TM-BE13 4.86 4.44 3.29 3.18 5.92 3.79 8.87 5.33 4.40 6.70 4.54 14.09 5.30 3.63

IsoL6/11 1.48 1.55 1.15 1.78 4.69 2.87 3.66 5.73 2.76 3.96 1.57 1.07 2.55 1.32 IP23 4.53 3.94 3.06 4.31 3.86 4.36 4.29 5.89 3.91 4.13 4.71 3.56 6.04 2.32

EA13/03 2.58 2.01 1.86 2.99 2.84 2.23 2.35 2.99 3.83 2.59 5.54 2.65 3.60 2.17 PA8 1.80 1.51 2.36 1.97 2.02 3.19 2.66 2.54 1.88 2.79 2.17 1.91 4.62 2.17 πTC13 3.93 4.37 6.24 7.89 8.37 8.76 8.12 8.34 6.69 7.85 5.14 5.32 11.45 4.84

HTBH38/08 1.89 2.01 2.36 3.71 4.86 6.87 7.71 6.09 4.15 6.96 1.44 1.31 5.26 1.25 NHTBH38/08 2.41 2.89 3.74 2.83 4.96 5.90 8.91 8.95 3.81 9.07 2.86 2.24 7.18 2.06

NCCE30 0.54 0.54 0.39 0.92 2.71 1.33 1.40 1.41 0.63 1.35 0.61 0.52 0.99 0.75 AE17 6.23 5.64 5.67 10.22 49.90 17.14 18.04 86.16 7.04 23.81 21.81 9.73 16.23 6.85

HC7/11 11.51 6.77 4.63 11.05 14.63 14.32 10.48 30.14 3.35 6.42 2.42 2.58 8.39 3.98 3dEE8 15.90 10.73 9.01 19.13 11.13 18.41 12.41 12.87 8.55 10.46 19.09 21.07 13.81 4.83

4dAEE5 6.30 9.34 7.57 6.03 4.30 11.91 5.19 7.07 6.58 5.11 11.04 11.05 9.45 0.88 pEE5 9.71 5.69 7.90 10.53 5.35 9.09 2.25 3.86 7.50 2.31 10.39 22.39 7.21 4.75

DC9/12 8.95 6.43 6.48 3.18 12.01 15.03 14.20 17.59 10.67 14.91 5.98 9.01 14.20 4.25 2pIsoE4 0.85 1.52 1.92 2.58 4.45 4.35 3.54 6.47 3.16 2.53 3.32 2.79 2.46 1.95 4pIsoE4 1.90 2.42 2.47 1.95 3.45 3.68 2.60 4.90 2.88 3.27 5.03 3.19 3.33 3.75

NGDWI21 0.10 0.03 0.16 0.26 0.21 0.15 0.17 0.16 0.13 0.17 0.57 0.37 0.08 0.02 MR-TMD-BE3 53.15 61.35 60.24 19.78 21.41 18.87 18.94 9.45 5.59 18.09 25.52 18.54 26.61 20.31

SMAE3 8.68 6.97 6.42 2.48 9.31 6.58 9.04 23.40 6.02 11.47 9.28 3.16 12.94 3.33

S6x6 0.82 1.07 0.31 2.52 7.84 4.17 3.38 3.52 0.80 3.19 1.51 1.13 1.82 1.72

ABDE13 0.81 1.11 1.50 1.92 9.00 9.73 10.67 14.60 5.35 9.01 3.36 1.96 6.61 4.62

S-13

Table S6. MUEs (kcal/mol) for the AME471 database and subdatabases: hybrid meta-GGAs (H meta-GGAs)

Type ———————————————————————————mGGAh———————————————————————————

Functional TPSSh τ-HCTHhyb BB1K MPWB1K MPW1B95 BMK TPSS1KCIS MPWKCIS1K MPW1KCIS PBE1KCIS PWB6K SR-MGM-BE9 3.34 2.41 4.31 3.78 2.65 2.55 4.25 6.25 4.05 3.64 3.85

SR-MGN-BE107 2.61 1.62 2.35 1.93 1.22 1.20 2.10 2.70 2.65 2.65 2.45 SR-TM-BE17 4.48 6.13 5.53 5.14 4.38 5.73 5.91 6.97 6.42 5.58 5.32

MR-MGM-BE4 6.93 5.72 8.89 19.99 6.73 9.56 9.39 17.67 10.28 15.85 13.2 MR-MGN-BE17 5.78 4.38 11.56 11.42 5.06 6.08 3.76 12.54 5.50 4.94 13.07 MR-TM-BE13 4.44 2.08 8.81 8.84 4.04 4.94 4.1 10.52 5.02 3.89 9.90

IsoL6/11 3.09 1.80 1.84 1.79 1.57 1.81 2.91 1.18 1.49 1.07 1.86 IP23 3.6 3.77 3.35 3.42 2.10 4.44 3.29 3.20 4.16 3.22 3.51

EA13/03 2.84 1.82 4.38 4.13 2.93 1.61 2.86 3.66 2.07 2.22 3.62 PA8 2.76 1.91 1.45 1.17 1.03 1.05 2.26 1.40 1.37 1.30 1.23 πTC13 8.06 7.45 5.99 5.68 5.38 4.58 7.49 6.11 5.55 5.03 5.85

HTBH38/08 5.96 5.28 1.18 1.3 3.01 1.27 4.69 1.63 5.86 5.13 1.28 NHTBH38/08 6.81 4.48 1.41 1.44 2.19 1.15 5.43 2.15 4.85 3.89 1.42

NCCE30 1.16 1.04 1.04 0.49 0.63 1.13 1.08 0.86 1.16 0.84 0.33 AE17 15.26 6.03 15.48 15.99 16.76 16.73 20.99 5.03 6.13 31.36 65.5

HC7/11 6.89 6.89 9.52 11.21 6.57 6.05 8.48 9.72 5.71 4.30 9.74 3dEE8 9.56 12.93 6.47 6.66 6.66 9.24 8.64 6.64 10.84 7.03 8.42

4dAEE5 5.13 7.92 8.62 4.63 4.59 5.93 5.27 10.02 9.48 9.30 4.83 pEE5 2.83 3.79 4.71 4.19 3.26 3.55 4.78 5.56 4.36 3.54 3.50

DC9/12 12.52 9.69 6.48 5.06 6.81 3.58 12.88 8.93 13.03 11.28 4.50 2pIsoE4 3.20 3.22 1.43 1.35 1.49 1.28 3.42 3.25 3.59 3.35 1.59 4pIsoE4 2.72 2.83 1.7 1.72 1.56 1.41 2.83 2.43 2.15 2.18 2.05

NGDWI21 0.17 0.17 0.35 0.14 0.15 0.68 0.14 0.17 0.19 0.10 0.11 MR-TMD-BE3 29.95 18.08 108.73 113.1 73.82 89.36 29.84 104.12 28.37 53.29 119.86

SMAE3 16.01 4.83 16.32 14.96 5.42 3.81 11.94 18.79 3.97 2.09 18.79

S6x6 3.58 2.92 2.70 1.71 2.08 2.71 3.34 3.12 3.83 3.27 1.16

ABDE13 9.88 4.85 1.66 1.18 1.20 1.21 8.33 4.04 5.44 3.46 1.33

S-14

Table S7. MUEs (kcal/mol) for the AME471 database and subdatabases: hybrid meta-GGAs (H meta-GGAs), RSH meta-GGA. NGA, GH-NGA

Type ———————————————————mGGAh——————————————————— mGGArsh mNGArsh mNGAh

Functional PW6B95 M05 M05-2X M06-HF M06 M06-2X M08-HX M08-SO M11 MN12-SX MN15 SR-MGM-BE9 12.93 3.24 2.18 6.06 3.57 2.01 2.52 2.29 5.04 7.03 2.72

SR-MGN-BE107 1.27 1.57 1.07 1.46 1.25 0.98 2.13 1.91 1.09 1.09 0.87 SR-TM-BE17 3.90 4.97 7.21 11.93 5.30 7.29 5.15 5.62 8.41 10.36 4.02

MR-MGM-BE4 7.62 6.36 7.26 14.38 5.00 10.45 7.77 10.05 11.16 9.15 3.92 MR-MGN-BE17 4.70 4.87 7.26 11.20 4.12 5.74 6.62 6.17 6.95 4.44 2.78 MR-TM-BE13 3.83 3.47 9.82 20.46 2.76 11.42 8.74 7.66 6.41 8.13 3.69

IsoL6/11 2.03 2.75 1.22 2.46 1.27 1.53 0.59 1.19 1.10 1.21 1.80 IP23 3.16 4.76 5.13 7.44 4.99 3.31 4.06 3.61 7.96 6.07 2.80

EA13/03 1.83 2.97 2.04 3.31 1.85 2.14 1.32 2.72 0.89 2.11 0.88 PA8 1.16 2.27 1.43 2.28 1.84 1.65 1.08 1.64 1.03 1.16 1.14 πTC13 5.82 5.69 3.06 2.05 4.40 1.49 1.87 1.84 2.24 3.24 3.52

HTBH38/08 3.13 1.94 1.35 2.07 1.98 1.14 0.72 1.07 1.30 0.95 0.97 NHTBH38/08 2.83 2.07 1.81 2.53 2.33 1.22 1.22 1.23 1.28 1.35 1.74

NCCE30 0.60 0.57 0.32 0.44 0.46 0.29 0.36 0.38 0.29 0.33 0.32 AE17 98.53 10.65 10.09 12.42 4.45 2.14 4.10 3.76 8.88 4.52 7.38

HC7/11 4.15 7.71 3.64 2.29 2.78 2.15 4.89 4.60 3.74 2.21 3.72 3dEE8 7.65 11.42 12.31 22.59 10.83 8.95 7.92 5.22 13.06 24.83 8.17

4dAEE5 4.92 9.65 8.81 12.06 7.86 9.44 6.61 6.20 6.43 16.76 5.28 pEE5 2.05 8.17 10.09 8.40 5.23 4.55 1.51 5.05 5.02 7.71 4.26

DC9/12 7.87 8.86 2.32 4.03 2.75 4.11 4.92 4.76 2.96 4.93 5.81 2pIsoE4 2.05 2.55 2.30 2.09 1.60 1.77 1.48 0.83 1.91 1.99 0.27 4pIsoE4 1.95 1.12 3.48 4.59 2.31 2.71 2.06 1.46 2.53 2.74 1.96

NGDWI21 0.12 0.08 0.07 0.13 0.19 0.11 0.09 0.08 0.14 0.27 0.02 MR-TMD-BE3 65.80 35.73 117.87 141.20 36.12 119.39 126.44 119.83 82.58 22.42 22.22

SMAE3 7.47 3.97 9.13 21.89 1.88 8.08 11.26 11.59 7.87 2.73 0.53

S6x6 1.93 2.16 0.90 0.83 1.12 0.54 0.53 0.60 0.63 1.29 0.32

ABDE13 2.73 6.48 1.69 5.11 2.29 1.38 1.27 1.81 2.25 1.59 1.80

S-15

Table S8. MUE (kcal/mol) for intermolecular charge transfer database (CT7)

Functionals CT7 Functionals CT7 SOGGA11-X 0.21 O3LYP 1.18 MPWB1K 0.23 TPSS1KCIS 1.23 MN15-L 0.25 revPBE 1.28 MN15 0.25 HCTH407 1.31 MGGA_MS2 0.26 HSE 1.31 PWB6K 0.26 RPBE 1.35 ωB97X-D 0.28 SOGGA11 1.35 M11 0.30 τ-HCTHhyb 1.38 M06-HF 0.35 MPW3LYP 1.38 M06-2X 0.37 BPW91 1.39 MN12-SX 0.40 TPSSh 1.44 BMK 0.43 OLYP 1.55 MPW1K 0.44 OreLYP 1.57 M05-2X 0.45 BLYP 1.67 MPW1B95 0.48 τ-HCTH 1.78 MPWKCIS1K 0.48 M06-L 1.78 CAM-B3LYP 0.48 MOHLYP 1.80 B97-3 0.49 N12 1.87 B1LYP 0.49 B97-D 1.89 B97-2 0.55 BP86 2.04 ωB97 0.56 TPSS 2.22 M08-HX 0.59 mPWPW 2.26 B3PW91 0.63 B86PW91 2.26 mPW1PW 0.66 MPWLYP1M 2.29 M08-SO 0.66 revTPSS 2.36 M05 0.66 TPSSLYP1W 2.36 BB1K 0.67 PBELYP1W 2.44 ωB97X 0.67 MPWLYP1W 2.45 PW6B95 0.70 PBE1W 2.51 MN12-L 0.70 B86LYP 2.83 B3LYP 0.71 VSXC 2.86 GAM 0.75 BR89LYP 2.87 HFLYP 0.87 PBE 2.97 LC-ωPBE 0.90 B86P86 3.11 B98 0.92 PW91 3.35 M11-L 0.94 HFPW91 3.84 MPW1KCIS 0.95 PBEsol 4.21 N12-SX 0.96 SOGGA 4.29 PBE1KCIS 0.99 MOHLYP2 5.29 PBE0 1.06 SVWN5 6.79 M06 1.07 SVWN3 7.00 B97-1 1.18

S-16

Table S9. MUE (kcal/mol) for Molecular Energy Databases and its subdatabases

Functionalsa MGBE150 TMBE33 BH76 NC87 EE18 IsoE14 HCTC20 AME454 AME471 MR54 SR313 GSVWN5 18.36 25.20 14.99 2.48 10.81 2.34 10.63 13.59 28.30 35.04 13.03 GSVWN3 20.33 27.79 15.08 2.64 9.25 2.37 11.25 15.39 26.02 38.42 15.02 SOGGA 8.63 15.00 11.28 1.61 8.08 1.88 8.90 7.90 17.83 22.32 7.22 PBEsol 8.81 14.50 11.28 1.63 8.81 1.80 7.39 7.88 16.47 21.92 7.25 SOGGA11 4.01 14.00 5.45 2.29 9.63 2.17 7.01 5.39 5.56 13.51 4.96 B86P86 4.67 27.10 7.86 2.00 8.22 2.40 8.95 6.80 7.63 20.52 5.84 B86LYP 4.48 25.41 7.02 2.39 9.73 3.92 13.47 6.72 7.38 20.95 5.55 BP86 5.55 9.05 8.94 2.43 7.32 2.71 7.29 6.13 6.52 14.06 5.86 BLYP 4.34 9.85 8.03 2.78 8.31 4.30 13.53 5.92 6.02 14.08 5.46 BR89LYP 4.10 6.55 6.82 1.96 8.74 4.82 13.99 5.44 6.27 11.33 5.43 B86PW91 4.33 7.41 6.23 2.51 7.12 2.34 9.33 4.96 5.68 9.76 4.89 PW91 5.04 10.26 9.20 1.49 7.41 2.38 5.32 5.70 5.66 14.25 5.46 BPW91 4.23 9.19 7.32 3.07 9.31 2.69 8.37 5.47 5.70 12.66 5.03 PBE 4.95 10.88 8.87 1.61 7.69 2.32 5.02 5.63 7.14 14.15 5.15 mPWPW 4.47 8.82 8.23 2.15 7.80 2.55 6.99 5.43 5.68 13.32 5.05 revPBE 4.25 7.64 6.70 3.04 7.15 2.85 9.43 5.26 5.47 11.44 4.88 RPBE 4.53 7.34 6.63 2.83 6.74 2.96 9.92 5.33 5.48 11.58 5.01 HCTH407 3.80 13.31 5.89 2.41 9.80 3.55 10.59 5.57 5.98 14.01 5.06 OLYP 3.75 8.42 5.44 4.32 7.56 3.22 11.32 5.25 5.43 11.03 4.59 MPWLYP1W 4.61 10.03 8.61 2.12 8.68 4.29 13.08 5.99 7.06 14.71 5.62 PBE1W 4.78 9.22 8.33 1.98 7.21 2.90 8.28 5.67 5.80 13.70 5.36 PBELYP1W 4.94 8.02 8.32 1.60 9.11 4.48 13.91 6.04 8.10 13.98 5.98 MOHLYP 7.20 10.14 5.65 5.03 7.32 3.86 13.26 7.04 16.03 19.76 5.45 B97-D 3.44 14.03 6.76 0.46 12.45 2.93 10.44 5.10 5.29 10.69 5.50 MOHLYP2 21.87 20.40 3.78 8.19 9.18 6.21 23.73 15.23 15.22 35.69 13.65 OreLYP 3.73 6.48 5.93 4.53 8.18 3.15 10.44 5.18 5.08 10.22 4.56 N12 3.42 9.36 6.90 2.30 16.22 2.21 7.09 5.05 5.38 9.35 5.20 GAM 2.97 6.24 5.25 1.14 6.93 3.29 7.77 4.17 4.39 9.45 4.11 VSXC 3.02 7.77 4.91 4.23 7.63 4.27 10.56 4.71 6.34 8.66 4.23 τ-HCTH 3.40 7.83 6.39 2.22 14.02 3.52 10.71 5.00 5.44 9.37 5.10 TPSS 3.47 8.36 8.31 1.92 7.58 3.32 8.95 4.98 5.46 9.48 4.97 TPSSLYP1W 5.20 6.65 7.52 1.98 8.76 5.70 15.97 6.00 8.89 12.16 6.11 M06-L 2.63 5.46 3.98 0.58 7.71 2.91 5.52 3.27 3.41 5.91 3.62 revTPSS 3.26 7.36 8.02 1.83 6.71 3.35 7.35 4.70 5.39 9.39 4.74 M11-L 2.81 7.02 2.15 0.97 14.44 3.06 4.19 3.45 4.11 6.74 3.71 MGGA_MS2 3.93 7.92 6.22 1.11 10.77 2.75 10.38 4.96 5.36 10.76 5.07 MN12-L 2.33 11.69 1.78 0.74 18.65 2.17 4.36 3.54 3.77 8.93 3.48 MN15-L 1.84 5.16 1.66 0.98 3.71 2.19 4.54 2.19 2.36 4.35 2.15 HFLYP 14.79 39.14 7.13 1.37 8.98 3.92 12.04 11.87 11.75 47.31 8.65 HFPW91 34.44 43.10 12.26 14.97 12.60 3.32 19.88 23.53 23.05 96.55 13.39 B3PW91 3.07 9.34 3.83 2.36 7.06 2.24 6.07 4.02 4.05 9.34 3.59 B3LYP 3.56 7.32 4.39 2.04 6.58 3.67 9.80 4.33 4.83 10.67 4.09 PBE0 2.82 10.18 3.83 1.33 6.85 1.87 7.26 3.72 4.98 10.37 3.28 mPW1PW 3.49 10.31 4.63 1.71 7.31 2.03 6.80 4.25 4.49 10.72 3.87 B1LYP 5.48 12.99 3.41 2.10 7.62 3.82 10.09 5.34 5.51 14.87 4.69 B98 2.71 6.92 3.74 1.51 7.16 2.55 7.60 3.50 3.55 8.26 3.28 B97-1 2.08 5.26 3.89 1.33 7.31 2.33 6.76 3.07 3.16 6.09 3.08 MPW1K 5.87 18.90 1.53 1.50 8.23 2.20 9.28 5.33 5.49 19.03 4.09 O3LYP 3.51 10.49 3.85 3.61 6.04 2.98 9.58 4.73 4.76 10.19 4.13 MPW3LYP 3.55 9.81 4.79 1.44 8.04 3.51 8.45 4.37 4.40 11.38 4.05 MPWLYP1M 3.82 6.27 7.83 1.87 8.18 4.07 11.68 5.08 5.33 10.90 5.03 B97-2 2.14 5.20 2.72 2.22 7.81 2.54 7.47 3.25 3.51 6.56 2.99 B97-3 2.50 9.85 1.83 2.10 6.20 2.56 7.44 3.44 3.57 9.92 2.70 SOGGA11-X 2.62 15.26 1.48 1.50 5.14 2.22 6.50 3.58 3.63 12.84 2.56

S-17

CAM-B3LYP 3.09 10.75 2.90 1.35 6.20 2.89 4.57 3.59 3.85 9.64 3.20 LC-ωPBE 3.47 12.43 1.77 1.56 8.46 1.55 8.96 4.02 4.79 11.81 3.39 HSE 2.97 9.92 3.98 1.31 8.09 1.99 6.60 3.85 4.89 10.18 3.54 ωB97 2.46 10.31 2.15 0.55 11.51 1.42 6.58 3.39 3.49 10.26 3.05 ωB97X 2.42 10.57 2.45 0.64 8.94 1.79 5.21 3.20 3.29 9.72 2.84 N12-SX 2.28 6.09 3.27 1.42 13.10 2.06 9.00 3.41 3.66 6.38 3.58 ωB97X-D 2.23 8.70 3.05 0.30 8.30 1.75 5.68 2.99 3.09 8.89 2.77 TPSSh 3.76 6.78 6.39 1.92 6.46 3.02 7.65 4.52 4.91 9.41 4.43 τ-HCTHhyb 2.37 5.62 4.88 1.61 9.00 2.50 7.25 3.57 3.66 6.38 3.68 BB1K 3.63 16.20 1.30 1.56 6.58 1.68 7.23 4.08 4.49 15.20 2.85 MPWB1K 3.53 16.41 1.37 0.91 5.41 1.64 7.62 3.88 4.31 16.17 2.58 MPW1B95 1.89 10.56 2.60 1.11 5.14 1.54 5.80 2.93 3.42 9.32 2.35 BMK 2.06 13.02 1.21 1.68 6.74 1.54 5.09 3.07 3.57 10.03 2.30 TPSS1KCIS 3.15 7.37 5.06 1.79 6.63 3.03 7.84 4.09 4.70 8.82 3.92 MPWKCIS1K 4.54 17.20 1.89 1.63 7.28 2.13 7.37 4.65 4.67 16.93 3.37 MPW1KCIS 3.50 7.86 5.36 2.03 8.66 2.28 5.61 4.25 4.32 8.81 4.09 PBE1KCIS 3.39 9.25 4.51 1.67 6.69 2.04 4.77 3.89 4.88 9.38 3.58 PWB6K 3.93 17.54 1.35 0.62 6.06 1.84 7.21 4.05 6.27 16.82 2.82 PW6B95 2.65 9.50 2.98 1.03 5.34 2.01 5.24 3.21 6.65 8.95 2.86 M05 2.60 7.18 2.01 1.11 10.03 2.23 6.40 3.24 3.51 7.24 3.16 M05-2X 2.06 18.30 1.58 0.50 10.72 2.17 3.26 3.46 3.70 13.25 2.61 M06-HF 3.50 27.04 2.30 0.53 15.72 2.96 2.13 5.15 5.42 19.90 4.01 M06 1.90 7.60 2.16 0.67 8.45 1.66 3.83 2.63 2.70 5.43 2.70 M06-2X 1.87 19.11 1.18 0.35 7.86 1.94 1.72 3.11 3.08 13.33 2.13 M08-HX 2.74 17.59 0.97 0.37 5.78 1.26 2.93 3.25 3.28 13.62 2.29 M08-SO 2.62 16.81 1.15 0.40 5.45 1.16 2.81 3.19 3.21 12.96 2.28 M11 2.36 14.36 1.29 0.39 8.99 1.74 2.77 3.20 3.41 10.35 2.80 MN12-SX 2.08 10.58 1.15 0.71 17.83 1.87 2.88 3.18 3.23 6.37 3.35 MN15 1.36 5.54 1.36 0.25 6.28 1.41 3.59 1.88 2.08 4.75 1.85

aThe functionals are in the same order as in Table S1.

S-18

Table S10. The average and median mean unsigned errors for the molecular energy database and its subdatabases calculated by 83 density functionals

MGBE150 TMBE33 BH76 EE18 IsoE14 HCTC20 AME471 Average MUE 4.68 12.02 5.02 8.52 2.69 8.11 6.21 Median MUE 3.50 9.85 4.63 7.86 2.40 7.44 4.98

NC87 MR54 SR313 AME454 AE17 AME471 Average MUE 1.96 13.89 4.59 5.16 34.28 6.21 Median MUE 1.63 10.76 4.09 4.52 10.88 4.98

S-19

Table S11. MUE (kcal/mol) for Molecular Energy Databases and its subdatabases

Functionalsa MGBE150 TMBE33 BH76 NC87 EE18 IsoE14 HCTC20 AME454 AME471 MR54 SR313 MN15 1.36 5.54 1.36 0.25 6.04 1.41 3.59 1.87 2.07 4.75 1.84 MN15-L 1.84 5.16 1.66 0.98 3.71 2.19 4.54 2.19 2.36 4.35 2.15 M06 1.90 7.60 2.16 0.67 8.45 1.66 3.83 2.63 2.70 5.43 2.70 M06-2X 1.87 19.11 1.18 0.35 7.86 1.94 1.72 3.11 3.08 13.33 2.13 ωB97X-D 2.23 8.70 3.05 0.30 8.30 1.75 5.68 2.99 3.09 8.89 2.77 B97-1 2.08 5.26 3.89 1.33 7.31 2.33 6.76 3.07 3.16 6.09 3.08 M08-SO 2.62 16.81 1.15 0.40 5.45 1.16 2.81 3.19 3.21 12.96 2.28 MN12-SX 2.08 10.58 1.15 0.71 17.83 1.87 2.88 3.18 3.23 6.37 3.35 M08-HX 2.74 17.59 0.97 0.37 5.78 1.26 2.93 3.25 3.28 13.62 2.29 ωB97X 2.42 10.57 2.45 0.64 8.94 1.79 5.21 3.20 3.29 9.72 2.84 M11 2.36 14.36 1.29 0.39 8.99 1.74 2.77 3.20 3.41 10.35 2.80 M06-L 2.63 5.46 3.98 0.58 7.71 2.91 5.52 3.27 3.41 5.91 3.62 MPW1B95 1.89 10.56 2.60 1.11 5.14 1.54 5.80 2.93 3.42 9.32 2.35 ωB97 2.46 10.31 2.15 0.55 11.51 1.42 6.58 3.39 3.49 10.26 3.05 M05 2.60 7.18 2.01 1.11 10.03 2.23 6.40 3.24 3.51 7.24 3.16 B97-2 2.14 5.20 2.72 2.22 7.81 2.54 7.47 3.25 3.51 6.56 2.99 B98 2.71 6.92 3.74 1.51 7.16 2.55 7.60 3.50 3.55 8.26 3.28 B97-3 2.50 9.85 1.83 2.10 6.20 2.56 7.44 3.44 3.57 9.92 2.70 BMK 2.06 13.02 1.21 1.68 6.74 1.54 5.09 3.07 3.57 10.03 2.30 SOGGA11-X 2.62 15.26 1.48 1.50 5.14 2.22 6.50 3.58 3.63 12.84 2.56 N12-SX 2.28 6.09 3.27 1.42 13.10 2.06 9.00 3.41 3.66 6.38 3.58 τ-HCTHhyb 2.37 5.62 4.88 1.61 9.00 2.50 7.25 3.57 3.66 6.38 3.68 M05-2X 2.06 18.30 1.58 0.50 10.72 2.17 3.26 3.46 3.70 13.25 2.61 MN12-L 2.33 11.69 1.78 0.74 18.65 2.17 4.36 3.54 3.77 8.93 3.48 CAM-B3LYP 3.09 10.75 2.90 1.35 6.20 2.89 4.57 3.59 3.85 9.64 3.20 B3PW91 3.07 9.34 3.83 2.36 7.06 2.24 6.07 4.02 4.05 9.34 3.59 M11-L 2.81 7.02 2.15 0.97 14.44 3.06 4.19 3.45 4.11 6.74 3.71 MPWB1K 3.53 16.41 1.37 0.91 5.41 1.64 7.62 3.88 4.31 16.17 2.58 MPW1KCIS 3.50 7.86 5.36 2.03 8.66 2.28 5.61 4.25 4.32 8.81 4.09 GAM 2.97 6.24 5.25 1.14 6.93 3.29 7.77 4.17 4.39 9.45 4.11 MPW3LYP 3.55 9.81 4.79 1.44 8.04 3.51 8.45 4.37 4.40 11.38 4.05 mPW1PW 3.49 10.31 4.63 1.71 7.31 2.03 6.80 4.25 4.49 10.72 3.87 BB1K 3.63 16.20 1.30 1.56 6.58 1.68 7.23 4.08 4.49 15.20 2.85 MPWKCIS1K 4.54 17.20 1.89 1.63 7.28 2.13 7.37 4.65 4.67 16.93 3.37 TPSS1KCIS 3.15 7.37 5.06 1.79 6.63 3.03 7.84 4.09 4.70 8.82 3.92 O3LYP 3.51 10.49 3.85 3.61 6.04 2.98 9.58 4.73 4.76 10.19 4.13 LC-ωPBE 3.47 12.43 1.77 1.56 8.46 1.55 8.96 4.02 4.79 11.81 3.39 PBE1KCIS 3.39 9.25 4.51 1.67 6.69 2.04 4.77 3.89 4.88 9.38 3.58 HSE 2.97 9.92 3.98 1.31 8.09 1.99 6.60 3.85 4.89 10.18 3.54 TPSSh 3.76 6.78 6.39 1.92 6.46 3.02 7.65 4.52 4.91 9.41 4.43 B3LYP 3.56 7.32 4.39 2.04 6.58 3.67 9.80 4.33 4.83 10.67 4.09 PBE0 2.82 10.18 3.83 1.33 6.85 1.87 7.26 3.72 4.98 10.37 3.28 OreLYP 3.73 6.48 5.93 4.53 8.18 3.15 10.44 5.18 5.08 10.22 4.56 B97-D 3.44 14.03 6.76 0.46 12.45 2.93 10.44 5.10 5.29 10.69 5.50 MPWLYP1M 3.82 6.27 7.83 1.87 8.18 4.07 11.68 5.08 5.33 10.90 5.03 TPSS 3.47 8.36 8.31 1.92 7.58 3.32 8.95 4.98 5.46 9.48 4.97 MGGA_MS2 3.93 7.92 6.22 1.11 10.77 2.75 10.38 4.96 5.36 10.76 5.07 N12 3.42 9.36 6.90 2.30 16.22 2.21 7.09 5.05 5.38 9.35 5.20 revTPSS 3.26 7.36 8.02 1.83 6.71 3.35 7.35 4.70 5.39 9.39 4.74 M06-HF 3.50 27.04 2.30 0.53 15.72 2.96 2.13 5.15 5.42 19.90 4.01 OLYP 3.75 8.42 5.44 4.32 7.56 3.22 11.32 5.25 5.43 11.03 4.59 τ-HCTH 3.40 7.83 6.39 2.22 14.02 3.52 10.71 5.00 5.44 9.37 5.10 revPBE 4.25 7.64 6.70 3.04 7.15 2.85 9.43 5.26 5.47 11.44 4.88 RPBE 4.53 7.34 6.63 2.83 6.74 2.96 9.92 5.33 5.48 11.58 5.01

S-20

MPW1K 5.87 18.90 1.53 1.50 8.23 2.20 9.28 5.33 5.49 19.03 4.09 B1LYP 5.48 12.99 3.41 2.10 7.62 3.82 10.09 5.34 5.51 14.87 4.69 SOGGA11 4.01 14.00 5.45 2.29 9.63 2.17 7.01 5.39 5.56 13.51 4.96 PW91 5.04 10.26 9.20 1.49 7.41 2.38 5.32 5.70 5.66 14.25 5.46 B86PW91 4.33 7.41 6.23 2.51 7.12 2.34 9.33 4.96 5.68 9.76 4.89 mPWPW 4.47 8.82 8.23 2.15 7.80 2.55 6.99 5.43 5.68 13.32 5.05 BPW91 4.23 9.19 7.32 3.07 9.31 2.69 8.37 5.47 5.70 12.66 5.03 PBE1W 4.78 9.22 8.33 1.98 7.21 2.90 8.28 5.67 5.80 13.70 5.36 HCTH407 3.80 13.31 5.89 2.41 9.80 3.55 10.59 5.57 5.98 14.01 5.06 BLYP 4.34 9.85 8.03 2.78 8.31 4.30 13.53 5.92 6.02 14.08 5.46 PWB6K 3.93 17.54 1.35 0.62 6.06 1.84 7.21 4.05 6.27 16.82 2.82 BR89LYP 4.10 6.55 6.82 1.96 8.74 4.82 13.99 5.44 6.27 11.33 5.43 VSXC 3.02 7.77 4.91 4.23 7.63 4.27 10.56 4.71 6.34 8.66 4.23 BP86 5.55 9.05 8.94 2.43 7.32 2.71 7.29 6.13 6.52 14.06 5.86 PW6B95 2.65 9.50 2.98 1.03 5.34 2.01 5.24 3.21 6.65 8.95 2.86 PBE 4.95 10.88 8.87 1.61 7.69 2.32 5.02 5.63 7.14 14.15 5.15 MPWLYP1W 4.61 10.03 8.61 2.12 8.68 4.29 13.08 5.99 7.06 14.71 5.62 B86LYP 4.48 25.41 7.02 2.39 9.73 3.92 13.47 6.72 7.38 20.95 5.55 B86P86 4.67 27.10 7.86 2.00 8.22 2.40 8.95 6.80 7.63 20.52 5.84 PBELYP1W 4.94 8.02 8.32 1.60 9.11 4.48 13.91 6.04 8.10 13.98 5.98 TPSSLYP1W 5.20 6.65 7.52 1.98 8.76 5.70 15.97 6.00 8.89 12.16 6.11 HFLYP 14.79 39.14 7.13 1.37 8.98 3.92 12.04 11.87 11.75 47.31 8.65 MOHLYP2 21.87 20.40 3.78 8.19 9.18 6.21 23.73 15.23 15.22 35.69 13.65 MOHLYP 7.20 10.14 5.65 5.03 7.32 3.86 13.26 7.04 16.03 19.76 5.45 PBEsol 8.81 14.50 11.28 1.63 8.81 1.80 7.39 7.88 16.47 21.92 7.25 SOGGA 8.63 15.00 11.28 1.61 8.08 1.88 8.90 7.90 17.83 22.32 7.22 HFPW91 34.44 43.10 12.26 14.97 12.60 3.32 19.88 23.53 23.05 96.55 13.39 GSVWN3 20.33 27.79 15.08 2.64 9.25 2.37 11.25 15.39 26.02 38.42 15.02 GSVWN5 18.36 25.20 14.99 2.48 10.81 2.34 10.63 13.59 28.30 35.04 13.03

aThe functionals are in the order of increase MUE of AME471

S-21

Table S12. MUE (kcal/mol) for the Molecular Structure Database (MS10)

Functionalsa DG4H DG6L MS10 Functionals DG4H DG6L MS10 GKSVWN5 0.031 0.011 0.019 PBE0 0.014 0.003 0.007 GKSVWN3 0.034 0.012 0.021 mPW1PW 0.015 0.003 0.008 SOGGA 0.013 0.009 0.011 B1LYP 0.032 0.009 0.018 PBEsol 0.011 0.010 0.010 B98 0.026 0.007 0.015 SOGGA11 0.054 0.008 0.026 B97-1 0.028 0.006 0.015 B86P86 0.029 0.015 0.021 MPW1K 0.012 0.011 0.011 B86LYP 0.045 0.024 0.032 O3LYP 0.030 0.004 0.014 BP86 0.021 0.015 0.017 B97-2 0.023 0.002 0.010 BLYP 0.037 0.019 0.026 MPW3LYP 0.026 0.009 0.016 BR89LYP 0.046 0.021 0.031 MPWLYP1M 0.031 0.018 0.023 B86PW91 0.031 0.014 0.021 B97-3 0.034 0.004 0.016 PW91 0.019 0.012 0.015 SOGGA11-X 0.021 0.004 0.011 BPW91 0.022 0.013 0.017 CAM-B3LYP 0.011 0.008 0.009 PBE 0.020 0.013 0.016 LC-wPBE 0.011 0.013 0.012 mPWPW 0.021 0.012 0.016 HSE 0.016 0.003 0.008 revPBE 0.034 0.015 0.023 ωB97 0.018 0.011 0.014 RPBE 0.038 0.016 0.025 ωB97X 0.017 0.008 0.012 HCTH407 0.033 0.004 0.016 N12-SX 0.012 0.005 0.008 OLYP 0.036 0.009 0.020 ωB97X-D 0.023 0.005 0.012 MPWLYP1W 0.037 0.020 0.027 TPSSh 0.013 0.006 0.009 PBE1W 0.028 0.014 0.020 τ-HCTHhyb 0.017 0.006 0.010 PBELYP1W 0.043 0.020 0.029 BB1K 0.011 0.009 0.010 MOHLYP 0.054 0.022 0.035 MPWB1K 0.010 0.012 0.011 B97-D 0.043 0.013 0.025 MPW1B95 0.011 0.005 0.007 MOHLYP2 0.092 0.022 0.050 BMK 0.028 0.007 0.015 OreLYP 0.034 0.011 0.020 TPSS1KCIS 0.019 0.005 0.011 N12 0.007 0.008 0.008 MPWKCIS1K 0.019 0.010 0.014 GAM 0.034 0.007 0.018 MPW1KCIS 0.025 0.006 0.014 VSXC 0.021 0.006 0.012 PBE1KCIS 0.024 0.003 0.011 τ-HCTH 0.019 0.006 0.011 PWB6K 0.012 0.013 0.013 TPSS 0.014 0.010 0.012 PW6B95 0.015 0.004 0.008 TPSSLYP1W 0.031 0.017 0.023 M05 0.031 0.007 0.017 M06-L 0.008 0.006 0.007 M05-2X 0.032 0.006 0.016 revTPSS 0.021 0.011 0.015 M06-HF 0.044 0.013 0.025 M11-L 0.022 0.012 0.016 M06 0.023 0.006 0.013 MGGA_MS2 0.008 0.007 0.007 M06-2X 0.049 0.004 0.022 MN12-L 0.022 0.005 0.012 M08-HX 0.047 0.005 0.022 MN15-L 0.014 0.004 0.008 M08-SO 0.027 0.007 0.015 HFLYP 0.031 0.046 0.040 M11 0.017 0.007 0.011 HFPW91 0.029 0.050 0.042 MN12-SX 0.017 0.003 0.009 B3PW91 0.017 0.004 0.009 MN15 0.008 0.005 0.006 B3LYP 0.027 0.009 0.016

aThe functionals listed are in the same order as in Table S1.

S-22

Table S13. MUE (kcal/mol) for the Molecular Structure Database (MS10)

Functionalsa DG4H DG6L MS10 Functionals DG4H DG6L MS10 MN15 0.008 0.005 0.006 B97-1 0.028 0.006 0.015 M06-L 0.008 0.006 0.007 BMK 0.028 0.007 0.015 MGGA_MS2 0.008 0.007 0.007 M08-SO 0.027 0.007 0.015 PBE0 0.014 0.003 0.007 PBE 0.020 0.013 0.016 MPW1B95 0.011 0.005 0.007 HCTH407 0.033 0.004 0.016 N12 0.007 0.008 0.008 mPWPW 0.021 0.012 0.016 MN15-L 0.014 0.004 0.008 M11-L 0.022 0.012 0.016 mPW1PW 0.015 0.003 0.008 B3LYP 0.027 0.009 0.016 HSE 0.016 0.003 0.008 MPW3LYP 0.026 0.009 0.016 N12-SX 0.012 0.005 0.008 B97-3 0.034 0.004 0.016 PW6B95 0.015 0.004 0.008 M05-2X 0.032 0.006 0.016 B3PW91 0.017 0.004 0.009 BP86 0.021 0.015 0.017 CAM-B3LYP 0.011 0.008 0.009 BPW91 0.022 0.013 0.017 TPSSh 0.013 0.006 0.009 M05 0.031 0.007 0.017 MN12-SX 0.017 0.003 0.009 GAM 0.034 0.007 0.018 PBEsol 0.011 0.010 0.010 B1LYP 0.032 0.009 0.018 B97-2 0.023 0.002 0.010 GKSVWN5 0.031 0.011 0.019 τ-HCTHhyb 0.017 0.006 0.010 OLYP 0.036 0.009 0.020 BB1K 0.011 0.009 0.010 PBE1W 0.028 0.014 0.020 SOGGA 0.013 0.009 0.011 OreLYP 0.034 0.011 0.020 τ-HCTH 0.019 0.006 0.011 GKSVWN3 0.034 0.012 0.021 MPW1K 0.012 0.011 0.011 B86P86 0.029 0.015 0.021 SOGGA11-X 0.021 0.004 0.011 B86PW91 0.031 0.014 0.021 MPWB1K 0.010 0.012 0.011 M06-2X 0.049 0.004 0.022 TPSS1KCIS 0.019 0.005 0.011 M08-HX 0.047 0.005 0.022 PBE1KCIS 0.024 0.003 0.011 revPBE 0.034 0.015 0.023 M11 0.017 0.007 0.011 TPSSLYP1W 0.031 0.017 0.023 VSXC 0.021 0.006 0.012 MPWLYP1M 0.031 0.018 0.023 TPSS 0.014 0.010 0.012 RPBE 0.038 0.016 0.025 MN12-L 0.022 0.005 0.012 B97-D 0.043 0.013 0.025 LC-wPBE 0.011 0.013 0.012 M06-HF 0.044 0.013 0.025 ωB97X 0.017 0.008 0.012 SOGGA11 0.054 0.008 0.026 ωB97X-D 0.023 0.005 0.012 BLYP 0.037 0.019 0.026 PWB6K 0.012 0.013 0.013 MPWLYP1W 0.037 0.020 0.027 M06 0.023 0.006 0.013 PBELYP1W 0.043 0.020 0.029 O3LYP 0.030 0.004 0.014 BR89LYP 0.046 0.021 0.031 ωB97 0.018 0.011 0.014 B86LYP 0.045 0.024 0.032 MPWKCIS1K 0.019 0.010 0.014 MOHLYP 0.054 0.022 0.035 MPW1KCIS 0.025 0.006 0.014 HFLYP 0.031 0.046 0.040 PW91 0.019 0.012 0.015 HFPW91 0.029 0.050 0.042 revTPSS 0.021 0.011 0.015 MOHLYP2 0.092 0.022 0.050 B98 0.026 0.007 0.015

aThe functionals listed are in the order of increasing MUE of MS10

S-23

Table S14. Geometries (in Å), charge, and multiplicity of species in several databases: alkyl bond dissociation energies (ABDE13), six dimers at six intermonomeric distances (S6x6 ), semiconductor band gaps (SBG31), and excitation energies of selected organic molecules (EE69)

ABDE13

butane 0 1

6 -0.928482 1.410876 0.001213 6 0.586226 1.393089 0.002419 1 -1.325379 2.425099 0.001662 1 -1.329631 0.903049 -0.876909 1 -1.331099 0.901704 0.877875 6 1.170559 -0.009541 -0.000211 1 0.964525 1.94072 -0.866061 1 0.963033 1.936803 0.874005 6 2.68526 -0.027337 0.000687 1 0.792474 -0.557052 0.868435 1 0.793529 -0.553314 -0.871656 1 3.082164 -1.041557 -0.001058 1 3.087694 0.482886 -0.875454 1 3.08662 0.479435 0.87932

c3h6 0 1

6 -2.213267 1.521683 0.026767 1 -2.534248 2.309355 -0.657553 1 -2.615002 0.576378 -0.334569 1 -2.683762 1.743549 0.986643 6 -0.733774 1.480744 0.147551 6 0.031525 0.439071 -0.141552 1 -0.259361 2.39089 0.505652 1 1.106943 0.470927 -0.031228 1 -0.389811 -0.492653 -0.501783

S-24

ch2chch2ch2 0 2 6 2.513982 -0.250375 -0.295934

6 1.482785 0.336378 0.292951 1 3.480077 0.230366 -0.370971 1 2.432749 -1.24237 -0.725684 1 1.600633 1.335169 0.704616 6 0.106889 -0.252384 0.412276 6 -0.896292 0.558103 -0.321381 1 -0.168588 -0.320092 1.467981 1 0.130613 -1.276718 0.028186 1 -1.518495 1.284484 0.182929 1 -0.8872 0.579974 -1.402943

ch2chch2 0 2

6 2.506597 -0.193407 -0.367482 6 1.434894 0.240846 0.377821 1 3.389989 0.413867 -0.503891 1 2.498586 -1.165757 -0.844876 1 1.506087 1.226516 0.82946 6 0.279877 -0.474051 0.59625 1 -0.530516 -0.079588 1.19245 1 0.145809 -1.462726 0.174454

ch2chchch2ch3 0 2 6 -1.94513 0.93024 -0.034904

1 -1.297993 0.412352 -0.731786 1 -3.005829 0.889974 -0.237078 6 -1.446735 1.604426 1.04933 6 -0.106833 1.712848 1.391443 1 -2.159234 2.097973 1.703228 1 0.151386 2.273896 2.284018 6 1.012184 1.103577 0.621485 6 2.38335 1.447258 1.168938 1 0.942277 1.409191 -0.428893 1 0.885785 0.014298 0.594468 1 3.178114 0.985385 0.586139 1 2.552744 2.523978 1.161466 1 2.49256 1.109416 2.199568

S-25

ch2ch 0 2

6 2.502688 -0.208688 -0.302027 6 1.498909 0.396916 0.259687 1 3.480137 0.259571 -0.421973 1 2.422208 -1.220921 -0.687327 1 1.308258 1.358232 0.708837

ch3 0 2

6 -1.273369 0.742196 -0.217501 1 -0.765914 -0.156538 0.092307 1 -0.765894 1.459855 -0.840918 1 -2.28985 0.921076 0.092307

ch3oco 0 2

6 -0.657339 0.161134 -0.000029 8 -0.703403 1.347083 -0.00013 8 -1.611924 -0.735153 0.000126 6 -2.966686 -0.202337 0.000154 1 -3.623447 -1.064623 0.001145 1 -3.123468 0.404176 0.889298 1 -3.124106 0.402576 -0.889968

chchch2ch3 0 2

6 1.896141 -0.029947 -0.336025 6 0.791764 -0.14031 0.350007 1 2.881819 -0.464537 -0.304987 1 0.759347 -0.83962 1.19256 6 -0.48429 0.598168 0.08652 6 -1.655563 -0.336905 -0.165507 1 -0.344787 1.273237 -0.758664 1 -0.707708 1.231069 0.950709 1 -2.580419 0.217792 -0.315916 1 -1.486574 -0.950834 -1.049405 1 -1.809993 -1.013146 0.675738

S-26

hcoo 0 2

6 -2.601901 1.269372 -0.016199 8 -1.353352 1.263053 -0.016452 8 -3.083478 2.421023 -0.015952 1 -3.214168 0.35471 -0.016149

hexene 0 1

6 2.775589 -0.346686 -0.122933 6 1.452569 -0.32747 0.629207 1 3.34058 0.569663 0.049988 1 3.401163 -1.182486 0.18772 1 2.616239 -0.429717 -1.197689 1 0.914187 -1.260154 0.455665 1 1.658835 -0.298898 1.704048 6 0.607652 0.847686 0.26793 6 -0.60859 0.846601 -0.270736 1 1.067994 1.813688 0.461946 1 -1.069333 1.811807 -0.467736 6 -1.452999 -0.330019 -0.628417 6 -2.776046 -0.347456 0.123711 1 -0.914236 -1.261936 -0.45196 1 -1.65922 -0.304866 -1.703353 1 -3.401256 -1.184474 -0.184385 1 -2.61672 -0.427094 1.198727 1 -3.341411 0.568118 -0.052074

S-27

mb 0 1

6 -5.65074 1.129488 -0.048426 6 -4.140196 1.036621 0.018568 1 -6.040176 0.628813 -0.939199 1 -6.118332 0.603684 0.788655 6 -3.648172 -0.3957 0.020929 1 -3.711582 1.585207 -0.821992 1 -3.789859 1.56121 0.909219 1 -2.561857 -0.446777 0.068792 1 -4.039005 -0.951324 0.874433 1 -3.960611 -0.927296 -0.878923 6 -6.161979 2.540342 -0.051048 8 -5.487943 3.535798 -0.005642 8 -7.51015 2.559874 -0.112332 6 -8.089029 3.863014 -0.119431 1 -9.163204 3.715922 -0.1692 1 -7.824578 4.410031 0.784498 1 -7.746327 4.435117 -0.980556

mf 0 1

6 -2.501938 1.226371 -0.016195 8 -1.320957 1.034671 -0.016142 8 -3.102706 2.421087 -0.016236 1 -3.277874 0.445166 -0.016157 6 -2.208181 3.538038 -0.016264 1 -2.833242 4.424561 -0.01645 1 -1.573549 3.521174 0.86821 1 -1.573321 3.520952 -0.90057

S-28

pentene 0 1

6 -4.74352 2.259537 0.437271 6 -3.660756 2.071534 -0.301942 1 -5.339084 3.159608 0.364659 1 -5.081759 1.513389 1.14754 1 -3.359835 2.852084 -0.99799 6 -2.779585 0.872125 -0.260052 6 -1.332277 1.200881 0.092731 1 -2.79296 0.377148 -1.238045 1 -3.178513 0.143641 0.451106 6 -0.433859 -0.018409 0.086861 1 -0.952972 1.946865 -0.611256 1 -1.305026 1.683218 1.072972 1 0.594074 0.234067 0.342604 1 -0.775325 -0.765739 0.804112 1 -0.420143 -0.496111 -0.893621

R1_oc=och2ch2ch3 0 2 6 0.725948 -0.574955 0.000031

6 1.877482 0.416106 -0.000504 1 0.77151 -1.239782 -0.866937 1 0.771642 -1.238909 0.867672 6 3.225933 -0.274045 0.000267 1 1.788489 1.070383 -0.869647 1 1.788164 1.071697 0.867612 1 4.041532 0.446264 -0.000266 1 3.348599 -0.907986 0.878967 1 3.348817 -0.909531 -0.877285 6 -0.618419 0.061543 -0.000202 8 -0.816041 1.300429 0.000035 8 -1.70118 -0.575127 -0.000079

S-29

R3_ch3ch2ch2 0 2 6 0.824777 -0.662196 -0.000008

6 1.901391 0.35202 -0.000535 1 0.49461 -1.124722 -0.92102 1 0.494497 -1.123611 0.921522 6 3.303116 -0.259952 0.000277 1 1.802231 1.001319 -0.874214 1 1.801818 1.002661 0.872102 1 4.07343 0.511295 -0.000107 1 3.457381 -0.885787 0.878801 1 3.457823 -0.887106 -0.877227

R4_ch3ch2 0 2

6 2.062986 0.609261 -0.000591 6 3.251699 -0.260586 0.000335 1 1.661019 1.006973 -0.922101 1 1.66087 1.008741 0.920089 1 4.188885 0.311584 -0.000244 1 3.289952 -0.900677 0.882293 1 3.289987 -0.902504 -0.880294

R4_ch3oc=och2 0 2 6 0.552927 -0.758415 -0.010219

1 0.571324 -1.776966 -0.368625 1 1.47441 -0.259591 0.245791 6 -0.682113 -0.038159 0.138083 8 -0.784949 1.104345 0.532865 8 -1.74748 -0.799312 -0.222572 6 -3.005185 -0.145109 -0.09957 1 -3.752917 -0.865008 -0.416773 1 -3.186157 0.158912 0.931069 1 -3.044559 0.743288 -0.729348

R5_ch3oc=och2ch2 0 2 6 0.674387 -0.448321 -0.000125

6 1.789643 0.51663 -0.000663 1 0.710236 -1.11217 -0.867614 1 0.710472 -1.111453 0.86791 1 2.128108 0.966574 -0.92265 1 2.128028 0.967675 0.920814

S-30

6 -0.697488 0.197738 -0.000176 8 -0.925163 1.376763 -0.000472 8 -1.656165 -0.750354 0.000189 6 -2.991927 -0.248458 0.00023 1 -3.640881 -1.118349 0.000987 1 -3.176098 0.361262 0.883585 1 -3.176597 0.360059 -0.883854

S-31

S6x6

04_Water-Peptide_0.90 0 1

O -0.392018453 -0.384718737 0.076071325 H -0.911460851 0.41381204 0.177648774 H 0.52490382 -0.068484694 0.090511364 C 2.05149617 -2.260917624 -0.227813599 H 2.701459013 -3.122029501 -0.360728986 H 1.3705202 -2.183445565 -1.071678874 H 1.438479272 -2.399713611 0.659194764 C 2.806228248 -0.962904747 -0.095220092 O 2.229512801 0.112390109 0.06136865 N 4.156861371 -1.060407431 -0.159838061 H 4.557812999 -1.97094141 -0.289353159 C 5.025103483 0.091563029 -0.050394979 H 4.388609353 0.959863472 0.084389628 H 5.69069299 0.000107831 0.805697902 H 5.619569206 0.220983518 -0.952654166




O -0.392018453 -0.384718737 0.076071325 H -0.911460851 0.41381204 0.177648774 H 0.52490382 -0.068484694 0.090511364

S-32

C 2.240786693 -2.240832146 -0.23104979 H 2.890749536 -3.101944023 -0.363965177 H 1.559810723 -2.163360087 -1.074915065 H 1.627769795 -2.379628133 0.655958573 C 2.995518771 -0.942819269 -0.098456283 O 2.418803324 0.132475587 0.058132459 N 4.346151894 -1.040321953 -0.163074252 H 4.747103522 -1.950855932 -0.29258935 C 5.214394006 0.111648507 -0.05363117 H 4.577899876 0.97994895 0.081153437 H 5.879983513 0.020193309 0.802461711 H 5.808859729 0.241068996 -0.955890357




O -0.392018453 -0.384718737 0.076071325 H -0.911460851 0.41381204 0.177648774 H 0.52490382 -0.068484694 0.090511364 C 2.430229786 -2.220730479 -0.234288589 H 3.080192629 -3.081842356 -0.367203976 H 1.749253816 -2.14325842 -1.078153864 H 1.817212888 -2.359526466 0.652719774 C 3.184961864 -0.922717602 -0.101695082 O 2.608246417 0.152577254 0.05489366 N 4.535594987 -1.020220286 -0.166313051

S-33

H 4.936546615 -1.930754265 -0.295828149 C 5.403837099 0.131750174 -0.056869969 H 4.767342969 1.000050617 0.077914638 H 6.069426606 0.040294976 0.799222912 H 5.998302822 0.261170663 -0.959129156



04_Water-Peptide_A 0 1

O -0.392018453 -0.384718737 0.076071325 H -0.911460851 0.41381204 0.177648774 H 0.52490382 -0.068484694 0.090511364

04_Water-Peptide_B 0 1

C 2.05149617 -2.260917624 -0.227813599 H 2.701459013 -3.122029501 -0.360728986 H 1.3705202 -2.183445565 -1.071678874 H 1.438479272 -2.399713611 0.659194764 C 2.806228248 -0.962904747 -0.095220092 O 2.229512801 0.112390109 0.06136865 N 4.156861371 -1.060407431 -0.159838061 H 4.557812999 -1.97094141 -0.289353159 C 5.025103483 0.091563029 -0.050394979 H 4.388609353 0.959863472 0.084389628 H 5.69069299 0.000107831 0.805697902

S-34

H 5.619569206 0.220983518 -0.952654166

17_Uracil-Uracil_BP_0.90 0 1

N -0.729999134 0.022767626 0.000914648 H 0.298422555 0.074004465 0.001623038 C -1.296824528 -1.24042682 0.001502336 O -0.594098857 -2.253517508 0.002633705 C -2.743622291 -1.262331701 0.000479378 H -3.249590454 -2.211835169 0.000833106 C -3.422019974 -0.095909207 -0.00092259 H -4.500897091 -0.049216027 -0.001745463 N -2.774836844 1.105408947 -0.001418075 H -3.283838068 1.973877391 -0.002485743 C -1.391478664 1.237019779 -0.000525382 O -0.839843713 2.31703528 -0.001001251 N 3.975452157 -1.076929522 0.000498413 H 4.42269594 -0.170356322 0.000885229 C 4.831499927 -2.191547312 -0.001001464 O 6.04095195 -2.039842897 -0.001750663 C 4.117281497 -3.45372085 -0.001505858 H 4.683866046 -4.3687516 -0.002644493 C 2.767112521 -3.457538722 -0.000545762 H 2.190149284 -4.370503488 -0.000864439 N 2.029121111 -2.306657883 0.00090465 H 1.002784851 -2.328100682 0.001581719 C 2.601892049 -1.061992842 0.001455297 O 1.951571165 -0.020774537 0.00269169


N -0.729999134 0.022767626 0.000914648 H 0.298422555 0.074004465 0.001623038 C -1.296824528 -1.24042682 0.001502336 O -0.594098857 -2.253517508 0.002633705 C -2.743622291 -1.262331701 0.000479378 H -3.249590454 -2.211835169 0.000833106 C -3.422019974 -0.095909207 -0.00092259 H -4.500897091 -0.049216027 -0.001745463 N -2.774836844 1.105408947 -0.001418075 H -3.283838068 1.973877391 -0.002485743 C -1.391478664 1.237019779 -0.000525382 O -0.839843713 2.31703528 -0.001001251

S-35

N 4.064139997 -1.081551127 0.000498868 H 4.51138378 -0.174977927 0.000885684 C 4.920187767 -2.196168917 -0.001001009 O 6.12963979 -2.044464502 -0.001750208 C 4.205969337 -3.458342455 -0.001505403 H 4.772553886 -4.373373205 -0.002644038 C 2.855800361 -3.462160327 -0.000545307 H 2.278837124 -4.375125093 -0.000863984 N 2.117808951 -2.311279488 0.000905105 H 1.091472691 -2.332722287 0.001582174 C 2.690579889 -1.066614447 0.001455752 O 2.040259005 -0.025396142 0.002692145




N -0.729999134 0.022767626 0.000914648

S-36

H 0.298422555 0.074004465 0.001623038 C -1.296824528 -1.24042682 0.001502336 O -0.594098857 -2.253517508 0.002633705 C -2.743622291 -1.262331701 0.000479378 H -3.249590454 -2.211835169 0.000833106 C -3.422019974 -0.095909207 -0.00092259 H -4.500897091 -0.049216027 -0.001745463 N -2.774836844 1.105408947 -0.001418075 H -3.283838068 1.973877391 -0.002485743 C -1.391478664 1.237019779 -0.000525382 O -0.839843713 2.31703528 -0.001001251 N 4.241515323 -1.090794319 0.000499777 H 4.688759106 -0.184221119 0.000886593 C 5.097563093 -2.205412109 -0.0010001 O 6.307015116 -2.053707694 -0.001749299 C 4.383344663 -3.467585647 -0.001504494 H 4.949929212 -4.382616397 -0.002643129 C 3.033175687 -3.471403519 -0.000544398 H 2.45621245 -4.384368285 -0.000863075 N 2.295184277 -2.32052268 0.000906014 H 1.268848017 -2.341965479 0.001583083 C 2.867955215 -1.075857639 0.001456661 O 2.217634331 -0.034639334 0.002693054


N -0.729999134 0.022767626 0.000914648 H 0.298422555 0.074004465 0.001623038 C -1.296824528 -1.24042682 0.001502336 O -0.594098857 -2.253517508 0.002633705 C -2.743622291 -1.262331701 0.000479378 H -3.249590454 -2.211835169 0.000833106 C -3.422019974 -0.095909207 -0.00092259 H -4.500897091 -0.049216027 -0.001745463 N -2.774836844 1.105408947 -0.001418075 H -3.283838068 1.973877391 -0.002485743 C -1.391478664 1.237019779 -0.000525382 O -0.839843713 2.31703528 -0.001001251 N 4.330202842 -1.095415907 0.000500232 H 4.777446625 -0.188842707 0.000887048 C 5.186250612 -2.210033697 -0.000999645 O 6.395702635 -2.058329282 -0.001748844 C 4.472032182 -3.472207235 -0.001504039

S-37

H 5.038616731 -4.387237985 -0.002642674 C 3.121863206 -3.476025107 -0.000543943 H 2.544899969 -4.388989873 -0.00086262 N 2.383871796 -2.325144268 0.000906469 H 1.357535536 -2.346587067 0.001583538 C 2.956642734 -1.080479227 0.001457116 O 2.30632185 -0.039260922 0.002693509



17_Uracil-Uracil_BP_A 0 1

N -0.729999134 0.022767626 0.000914648 H 0.298422555 0.074004465 0.001623038 C -1.296824528 -1.24042682 0.001502336 O -0.594098857 -2.253517508 0.002633705 C -2.743622291 -1.262331701 0.000479378 H -3.249590454 -2.211835169 0.000833106

S-38

C -3.422019974 -0.095909207 -0.00092259 H -4.500897091 -0.049216027 -0.001745463 N -2.774836844 1.105408947 -0.001418075 H -3.283838068 1.973877391 -0.002485743 C -1.391478664 1.237019779 -0.000525382 O -0.839843713 2.31703528 -0.001001251

17_Uracil-Uracil_BP_B 0 1

N 3.975452157 -1.076929522 0.000498413 H 4.42269594 -0.170356322 0.000885229 C 4.831499927 -2.191547312 -0.001001464 O 6.04095195 -2.039842897 -0.001750663 C 4.117281497 -3.45372085 -0.001505858 H 4.683866046 -4.3687516 -0.002644493 C 2.767112521 -3.457538722 -0.000545762 H 2.190149284 -4.370503488 -0.000864439 N 2.029121111 -2.306657883 0.00090465 H 1.002784851 -2.328100682 0.001581719 C 2.601892049 -1.061992842 0.001455297 O 1.951571165 -0.020774537 0.00269169

20_AcOH-AcOH_0.90 0 1

C -1.061709204 1.297140572 0.292060003 O -0.358161116 2.270458613 0.531812668 O -0.589303516 0.094917758 0.003788813 H 0.404435659 0.127722621 0.018411838 C -2.558427798 1.342549823 0.29625732 H -2.895997978 2.347464002 0.51831634 H -2.932889278 1.022390451 -0.672995551 H -2.93721196 0.644910433 1.039557084 C 2.630513912 1.107716378 0.269968222 O 1.926895547 0.13440189 0.03018062 O 2.158087578 2.310151766 0.557746693 H 1.164299038 2.277253532 0.543346189 C 4.12722636 1.061813632 0.268003827 H 4.464805924 0.060494439 0.030478332 H 4.508724905 1.772166571 -0.461465071 H 4.498742671 1.364508149 1.244059188

S-39

20_AcOH-AcOH_0.95 0 1


20_AcOH-AcOH_1.00 0 1


20_AcOH-AcOH_1.05 0 1

C -1.061709204 1.297140572 0.292060003 O -0.358161116 2.270458613 0.531812668 O -0.589303516 0.094917758 0.003788813

S-40

H 0.404435659 0.127722621 0.018411838 C -2.558427798 1.342549823 0.29625732 H -2.895997978 2.347464002 0.51831634 H -2.932889278 1.022390451 -0.672995551 H -2.93721196 0.644910433 1.039557084 C 2.884240499 1.108839153 0.271909953 O 2.180622134 0.135524665 0.032122351 O 2.411814165 2.311274541 0.559688424 H 1.418025625 2.278376307 0.54528792 C 4.380952947 1.062936407 0.269945558 H 4.718532511 0.061617214 0.032420063 H 4.762451492 1.773289346 -0.45952334 H 4.752469258 1.365630924 1.246000919

20_AcOH-AcOH_1.10 0 1


20_AcOH-AcOH_1.25 0 1

C -1.061709204 1.297140572 0.292060003 O -0.358161116 2.270458613 0.531812668 O -0.589303516 0.094917758 0.003788813 H 0.404435659 0.127722621 0.018411838 C -2.558427798 1.342549823 0.29625732 H -2.895997978 2.347464002 0.51831634 H -2.932889278 1.022390451 -0.672995551 H -2.93721196 0.644910433 1.039557084

S-41

C 3.222542615 1.110336186 0.274498927 O 2.51892425 0.137021698 0.034711325 O 2.750116281 2.312771574 0.562277398 H 1.756327741 2.27987334 0.547876894 C 4.719255063 1.06443344 0.272534532 H 5.056834627 0.063114247 0.035009037 H 5.100753608 1.774786379 -0.456934366 H 5.090771374 1.367127957 1.248589893

20_AcOH-AcOH_A 0 1

C -1.061709204 1.297140572 0.292060003 O -0.358161116 2.270458613 0.531812668 O -0.589303516 0.094917758 0.003788813 H 0.404435659 0.127722621 0.018411838 C -2.558427798 1.342549823 0.29625732 H -2.895997978 2.347464002 0.51831634 H -2.932889278 1.022390451 -0.672995551 H -2.93721196 0.644910433 1.039557084

20_AcOH-AcOH_B 0 1

C 2.630513912 1.107716378 0.269968222 O 1.926895547 0.13440189 0.03018062 O 2.158087578 2.310151766 0.557746693 H 1.164299038 2.277253532 0.543346189 C 4.12722636 1.061813632 0.268003827 H 4.464805924 0.060494439 0.030478332 H 4.508724905 1.772166571 -0.461465071 H 4.498742671 1.364508149 1.244059188

28_Benzene-Uracil_pi-pi_0.90 0 1

C 0.825769105 1.236524837 -0.040250437 H 1.521013168 2.063125196 -0.082471448 C 1.300159924 -0.062940879 0.127256013 H 2.363657528 -0.242261131 0.207674197 C 0.403523117 -1.128552182 0.198244857 H 0.773753376 -2.137426768 0.324121091 C -0.967809494 -0.895190489 0.103139941 H -1.665209 -1.719983422 0.160427446 C -1.443508379 0.404483279 -0.062441302 H -2.507511245 0.585501124 -0.124150163

S-42

C -0.545755493 1.468768748 -0.136247408 H -0.914221904 2.477422201 -0.267855164 N -0.287522703 0.707122355 2.884899047 H -0.660830096 1.608883785 2.622006076 C 1.104623979 0.634135449 3.016912386 O 1.795534298 1.628559141 2.872078321 C 1.583524093 -0.69994226 3.335022588 H 2.640576187 -0.852158199 3.469143724 C 0.703814866 -1.714323436 3.461239113 H 1.009742387 -2.722744045 3.697763474 N -0.641431021 -1.529291516 3.29114697 H -1.290178852 -2.291850459 3.390016141 C -1.21587933 -0.304490488 2.991732354 O -2.413667742 -0.153667213 2.849620162


C 0.825769105 1.236524837 -0.040250437 H 1.521013168 2.063125196 -0.082471448 C 1.300159924 -0.062940879 0.127256013 H 2.363657528 -0.242261131 0.207674197 C 0.403523117 -1.128552182 0.198244857 H 0.773753376 -2.137426768 0.324121091 C -0.967809494 -0.895190489 0.103139941 H -1.665209 -1.719983422 0.160427446 C -1.443508379 0.404483279 -0.062441302 H -2.507511245 0.585501124 -0.124150163 C -0.545755493 1.468768748 -0.136247408 H -0.914221904 2.477422201 -0.267855164 N -0.281657184 0.690635265 3.03974698 H -0.654964577 1.592396695 2.776854009 C 1.110489498 0.617648359 3.171760319 O 1.801399817 1.612072051 3.026926254 C 1.589389612 -0.71642935 3.489870521 H 2.646441706 -0.868645289 3.623991657 C 0.709680385 -1.730810526 3.616087046 H 1.015607906 -2.739231135 3.852611407 N -0.635565502 -1.545778606 3.445994903 H -1.284313333 -2.308337549 3.544864074 C -1.210013811 -0.320977578 3.146580287 O -2.407802223 -0.170154303 3.004468095

S-43




C 0.825769105 1.236524837 -0.040250437 H 1.521013168 2.063125196 -0.082471448 C 1.300159924 -0.062940879 0.127256013 H 2.363657528 -0.242261131 0.207674197 C 0.403523117 -1.128552182 0.198244857 H 0.773753376 -2.137426768 0.324121091 C -0.967809494 -0.895190489 0.103139941 H -1.665209 -1.719983422 0.160427446 C -1.443508379 0.404483279 -0.062441302 H -2.507511245 0.585501124 -0.124150163 C -0.545755493 1.468768748 -0.136247408 H -0.914221904 2.477422201 -0.267855164 N -0.269951039 0.657731056 3.348785671 H -0.643258432 1.559492486 3.0858927

S-44

C 1.122195643 0.58474415 3.48079901 O 1.813105962 1.579167842 3.335964945 C 1.601095757 -0.749333559 3.798909212 H 2.658147851 -0.901549498 3.933030348 C 0.72138653 -1.763714735 3.925125737 H 1.027314051 -2.772135344 4.161650098 N -0.623859357 -1.578682815 3.755033594 H -1.272607188 -2.341241758 3.853902765 C -1.198307666 -0.353881787 3.455618978 O -2.396096078 -0.203058512 3.313506786




C 0.825769105 1.236524837 -0.040250437 H 1.521013168 2.063125196 -0.082471448 C 1.300159924 -0.062940879 0.127256013

S-45

H 2.363657528 -0.242261131 0.207674197 C 0.403523117 -1.128552182 0.198244857 H 0.773753376 -2.137426768 0.324121091 C -0.967809494 -0.895190489 0.103139941 H -1.665209 -1.719983422 0.160427446 C -1.443508379 0.404483279 -0.062441302 H -2.507511245 0.585501124 -0.124150163 C -0.545755493 1.468768748 -0.136247408 H -0.914221904 2.477422201 -0.267855164 N -0.24660989 0.592122605 3.964984948 H -0.619917283 1.493884035 3.702091977 C 1.145536792 0.519135699 4.096998287 O 1.836447111 1.513559391 3.952164222 C 1.624436906 -0.81494201 4.415108489 H 2.681489 -0.967157949 4.549229625 C 0.744727679 -1.829323186 4.541325014 H 1.0506552 -2.837743795 4.777849375 N -0.600518208 -1.644291266 4.371232871 H -1.249266039 -2.406850209 4.470102042 C -1.174966517 -0.419490238 4.071818255 O -2.372754929 -0.268666963 3.929706063

28_Benzene-Uracil_pi-pi_A 0 1

C 0.825769105 1.236524837 -0.040250437 H 1.521013168 2.063125196 -0.082471448 C 1.300159924 -0.062940879 0.127256013 H 2.363657528 -0.242261131 0.207674197 C 0.403523117 -1.128552182 0.198244857 H 0.773753376 -2.137426768 0.324121091 C -0.967809494 -0.895190489 0.103139941 H -1.665209 -1.719983422 0.160427446 C -1.443508379 0.404483279 -0.062441302 H -2.507511245 0.585501124 -0.124150163 C -0.545755493 1.468768748 -0.136247408 H -0.914221904 2.477422201 -0.267855164

28_Benzene-Uracil_pi-pi_B 0 1

N -0.287522703 0.707122355 2.884899047 H -0.660830096 1.608883785 2.622006076 C 1.104623979 0.634135449 3.016912386 O 1.795534298 1.628559141 2.872078321

S-46

C 1.583524093 -0.69994226 3.335022588 H 2.640576187 -0.852158199 3.469143724 C 0.703814866 -1.714323436 3.461239113 H 1.009742387 -2.722744045 3.697763474 N -0.641431021 -1.529291516 3.29114697 H -1.290178852 -2.291850459 3.390016141 C -1.21587933 -0.304490488 2.991732354 O -2.413667742 -0.153667213 2.849620162

29_Pyridine-Uracil_pi-pi_0.90 0 1

N 1.210755335 0.028675778 0.329711113 C 0.61193497 -1.158449011 0.153451764 H 1.251477905 -2.029523404 0.219292947 C -0.75131399 -1.308649559 -0.088834071 H -1.170415774 -2.296869318 -0.213383204 C -1.54786767 -0.169940268 -0.156466912 H -2.611012747 -0.245954694 -0.338755744 C -0.943622374 1.070636117 0.019823098 H -1.518814305 1.984500285 -0.011644028 C 0.42771857 1.116108629 0.257348792 H 0.924694513 2.068051734 0.397547985 N -0.746112695 -0.302816882 2.92822204 H -1.641001714 -0.734680373 2.743618552 C -0.745857809 1.09499291 3.021233041 O -1.785740886 1.723192713 2.906382911 C 0.573636944 1.654074255 3.248796108 H 0.67495331 2.721296425 3.344664289 C 1.643510535 0.835381953 3.320316161 H 2.647389575 1.204046651 3.468742694 N 1.525449394 -0.521911311 3.207761497 H 2.338885388 -1.114098661 3.199593858 C 0.325002457 -1.169143739 2.9813798 O 0.23286521 -2.374561815 2.847800521


N 1.210755335 0.028675778 0.329711113 C 0.61193497 -1.158449011 0.153451764 H 1.251477905 -2.029523404 0.219292947 C -0.75131399 -1.308649559 -0.088834071 H -1.170415774 -2.296869318 -0.213383204 C -1.54786767 -0.169940268 -0.156466912

S-47

H -2.611012747 -0.245954694 -0.338755744 C -0.943622374 1.070636117 0.019823098 H -1.518814305 1.984500285 -0.011644028 C 0.42771857 1.116108629 0.257348792 H 0.924694513 2.068051734 0.397547985 N -0.73036703 -0.293799387 3.104724539 H -1.625256049 -0.725662878 2.920121051 C -0.730112144 1.104010405 3.19773554 O -1.769995221 1.732210208 3.08288541 C 0.589382609 1.66309175 3.425298607 H 0.690698975 2.73031392 3.521166788 C 1.6592562 0.844399448 3.49681866 H 2.66313524 1.213064146 3.645245193 N 1.541195059 -0.512893816 3.384263996 H 2.354631053 -1.105081166 3.376096357 C 0.340748122 -1.160126244 3.157882299 O 0.248610875 -2.36554432 3.02430302



S-48




N 1.210755335 0.028675778 0.329711113 C 0.61193497 -1.158449011 0.153451764 H 1.251477905 -2.029523404 0.219292947 C -0.75131399 -1.308649559 -0.088834071 H -1.170415774 -2.296869318 -0.213383204 C -1.54786767 -0.169940268 -0.156466912 H -2.611012747 -0.245954694 -0.338755744 C -0.943622374 1.070636117 0.019823098 H -1.518814305 1.984500285 -0.011644028 C 0.42771857 1.116108629 0.257348792 H 0.924694513 2.068051734 0.397547985 N -0.684223014 -0.26737285 3.621980149 H -1.579112033 -0.699236341 3.437376661 C -0.683968128 1.130436942 3.71499115

S-49

O -1.723851205 1.758636745 3.60014102 C 0.635526625 1.689518287 3.942554217 H 0.736842991 2.756740457 4.038422398 C 1.705400216 0.870825985 4.01407427 H 2.709279256 1.239490683 4.162500803 N 1.587339075 -0.486467279 3.901519606 H 2.400775069 -1.078654629 3.893351967 C 0.386892138 -1.133699707 3.675137909 O 0.294754891 -2.339117783 3.54155863



29_Pyridine-Uracil_pi-pi_A 0 1

N 1.210755335 0.028675778 0.329711113 C 0.61193497 -1.158449011 0.153451764 H 1.251477905 -2.029523404 0.219292947 C -0.75131399 -1.308649559 -0.088834071 H -1.170415774 -2.296869318 -0.213383204

S-50

C -1.54786767 -0.169940268 -0.156466912 H -2.611012747 -0.245954694 -0.338755744 C -0.943622374 1.070636117 0.019823098 H -1.518814305 1.984500285 -0.011644028 C 0.42771857 1.116108629 0.257348792 H 0.924694513 2.068051734 0.397547985

29_Pyridine-Uracil_pi-pi_B 0 1

N -0.746112695 -0.302816882 2.92822204 H -1.641001714 -0.734680373 2.743618552 C -0.745857809 1.09499291 3.021233041 O -1.785740886 1.723192713 2.906382911 C 0.573636944 1.654074255 3.248796108 H 0.67495331 2.721296425 3.344664289 C 1.643510535 0.835381953 3.320316161 H 2.647389575 1.204046651 3.468742694 N 1.525449394 -0.521911311 3.207761497 H 2.338885388 -1.114098661 3.199593858 C 0.325002457 -1.169143739 2.9813798 O 0.23286521 -2.374561815 2.847800521

47_Benzene-Benzene_TS_0.90 0 1

C 0.729188666 1.113101217 0.326728253 H 1.303215897 2.014222336 0.15916027 C 1.375087369 -0.119366352 0.412776946 H 2.450514736 -0.174623998 0.313307203 C 0.635039807 -1.280553386 0.629385409 H 1.136334479 -2.236017467 0.700217157 C -0.750985629 -1.209654296 0.757890338 H -1.324525898 -2.111412827 0.924198912 C -1.39703443 0.022670814 0.673089633 H -2.472425369 0.07848826 0.773997991 C -0.656897314 1.184296216 0.458338585 H -1.157828445 2.140587131 0.395096082 C 0.115547135 0.090530573 3.721571936 H 0.237673542 0.316014029 2.671145502 C -0.975534433 -0.664368038 4.148908205 H -1.696038962 -1.020882295 3.425213784 C -1.136234414 -0.958493361 5.501858272 H -1.983342001 -1.544461925 5.832105813 C -0.204351853 -0.497439981 6.43035235

S-51

H -0.328245349 -0.725406142 7.480359849 C 0.887233246 0.257662073 6.005112066 H 1.610352331 0.615495253 6.72549472 C 1.04603714 0.551147092 4.651620749 H 1.893295058 1.137221887 4.321573424


C 0.729188666 1.113101217 0.326728253 H 1.303215897 2.014222336 0.15916027 C 1.375087369 -0.119366352 0.412776946 H 2.450514736 -0.174623998 0.313307203 C 0.635039807 -1.280553386 0.629385409 H 1.136334479 -2.236017467 0.700217157 C -0.750985629 -1.209654296 0.757890338 H -1.324525898 -2.111412827 0.924198912 C -1.39703443 0.022670814 0.673089633 H -2.472425369 0.07848826 0.773997991 C -0.656897314 1.184296216 0.458338585 H -1.157828445 2.140587131 0.395096082 C 0.134572645 0.11840774 3.884432701 H 0.256699052 0.343891196 2.834006267 C -0.956508923 -0.636490871 4.31176897 H -1.677013452 -0.993005128 3.588074549 C -1.117208904 -0.930616194 5.664719037 H -1.964316491 -1.516584758 5.994966578 C -0.185326343 -0.469562814 6.593213115 H -0.309219839 -0.697528975 7.643220614 C 0.906258756 0.28553924 6.167972831 H 1.629377841 0.64337242 6.888355485 C 1.06506265 0.579024259 4.814481514 H 1.912320568 1.165099054 4.484434189


C 0.729188666 1.113101217 0.326728253 H 1.303215897 2.014222336 0.15916027 C 1.375087369 -0.119366352 0.412776946 H 2.450514736 -0.174623998 0.313307203 C 0.635039807 -1.280553386 0.629385409 H 1.136334479 -2.236017467 0.700217157 C -0.750985629 -1.209654296 0.757890338 H -1.324525898 -2.111412827 0.924198912

S-52

C -1.39703443 0.022670814 0.673089633 H -2.472425369 0.07848826 0.773997991 C -0.656897314 1.184296216 0.458338585 H -1.157828445 2.140587131 0.395096082 C 0.153204042 0.145707432 4.043919807 H 0.275330449 0.371190888 2.993493373 C -0.937877526 -0.609191179 4.471256076 H -1.658382055 -0.965705436 3.747561655 C -1.098577507 -0.903316502 5.824206143 H -1.945685094 -1.489285066 6.154453684 C -0.166694946 -0.442263122 6.752700221 H -0.290588442 -0.670229283 7.80270772 C 0.924890153 0.312838932 6.327459937 H 1.648009238 0.670672112 7.047842591 C 1.083694047 0.606323951 4.97396862 H 1.930951965 1.192398746 4.643921295



S-53




C 0.729188666 1.113101217 0.326728253 H 1.303215897 2.014222336 0.15916027 C 1.375087369 -0.119366352 0.412776946 H 2.450514736 -0.174623998 0.313307203 C 0.635039807 -1.280553386 0.629385409 H 1.136334479 -2.236017467 0.700217157 C -0.750985629 -1.209654296 0.757890338 H -1.324525898 -2.111412827 0.924198912 C -1.39703443 0.022670814 0.673089633 H -2.472425369 0.07848826 0.773997991 C -0.656897314 1.184296216 0.458338585 H -1.157828445 2.140587131 0.395096082 C 0.24277343 0.276949158 4.810645059

S-54

H 0.364899837 0.502432614 3.760218625 C -0.848308138 -0.477949453 5.237981328 H -1.568812667 -0.83446371 4.514286907 C -1.009008119 -0.772074776 6.590931395 H -1.856115706 -1.35804334 6.921178936 C -0.077125558 -0.311021396 7.519425473 H -0.201019054 -0.538987557 8.569432972 C 1.014459541 0.444080658 7.094185189 H 1.737578626 0.801913838 7.814567843 C 1.173263435 0.737565677 5.740693872 H 2.020521353 1.323640472 5.410646547

47_Benzene-Benzene_TS_A 0 1

C 0.729188666 1.113101217 0.326728253 H 1.303215897 2.014222336 0.15916027 C 1.375087369 -0.119366352 0.412776946 H 2.450514736 -0.174623998 0.313307203 C 0.635039807 -1.280553386 0.629385409 H 1.136334479 -2.236017467 0.700217157 C -0.750985629 -1.209654296 0.757890338 H -1.324525898 -2.111412827 0.924198912 C -1.39703443 0.022670814 0.673089633 H -2.472425369 0.07848826 0.773997991 C -0.656897314 1.184296216 0.458338585 H -1.157828445 2.140587131 0.395096082

47_Benzene-Benzene_TS_B 0 1

C 0.115547135 0.090530573 3.721571936 H 0.237673542 0.316014029 2.671145502 C -0.975534433 -0.664368038 4.148908205 H -1.696038962 -1.020882295 3.425213784 C -1.136234414 -0.958493361 5.501858272 H -1.983342001 -1.544461925 5.832105813 C -0.204351853 -0.497439981 6.43035235 H -0.328245349 -0.725406142 7.480359849 C 0.887233246 0.257662073 6.005112066 H 1.610352331 0.615495253 6.72549472 C 1.04603714 0.551147092 4.651620749 H 1.893295058 1.137221887 4.321573424

S-55

SBG31

AlAs 0 1

Al 0.00000 0.00000 0.00000 As 1.41520 1.41520 1.41520 -2 0.00000 2.83050 2.83050 -2 2.83050 0.00000 2.83050 -2 2.83050 2.83050 0.00000

AlP 0 1

Al 0.00000 0.00000 0.00000 P 1.36580 1.36580 1.36580

-2 0.00000 2.73150 2.73150 -2 2.73150 0.00000 2.73150 -2 2.73150 2.73150 0.00000

AlSb 0 1

Al 0.00000 0.00000 0.00000 Sb 1.53400 1.53400 1.53400 -2 0.00000 3.06800 3.06800 -2 3.06800 0.00000 3.06800 -2 3.06800 3.06800 0.00000

BaS 0 1

Ba 0.00000 0.00000 0.00000 S 3.19500 3.19500 3.19500

-2 0.00000 3.19500 3.19500 -2 3.19500 0.00000 3.19500 -2 3.19500 3.19500 0.00000

B-As 0 1

B 0.00000 0.00000 0.00000 As 1.19430 1.19430 1.19430 -2 0.00000 2.38850 2.38850 -2 2.38850 0.00000 2.38850 -2 2.38850 2.38850 0.00000

S-56

BaSe 0 1

Ba 0.00000 0.00000 0.00000 Se 3.29700 3.29700 3.29700 -2 0.00000 3.29700 3.29700 -2 3.29700 0.00000 3.29700 -2 3.29700 3.29700 0.00000

BaTe 0 1

Ba 0.00000 0.00000 0.00000 Te 3.50300 3.50300 3.50300 -2 0.00000 3.50300 3.50300 -2 3.50300 0.00000 3.50300 -2 3.50300 3.50300 0.00000

BP 0 1

B 0.00000 0.00000 0.00000 P 1.13730 1.13730 1.13730

-2 0.00000 2.27450 2.27450 -2 2.27450 0.00000 2.27450 -2 2.27450 2.27450 0.00000

C 0 1

C 0.00000 0.00000 0.00000 C 0.88750 0.88750 0.88750 -2 0.00000 1.77500 1.77500 -2 1.77500 0.00000 1.77500 -2 1.77500 1.77500 0.00000

CdS 0 1

Cd 0.00000 0.00000 0.00000 S 1.45450 1.45450 1.45450

-2 0.00000 2.90900 2.90900 -2 2.90900 0.00000 2.90900 -2 2.90900 2.90900 0.00000

CdSe 0 1

Cd 0.00000 0.00000 0.00000

S-57

Se 1.51300 1.51300 1.51300 -2 0.00000 3.02600 3.02600 -2 3.02600 0.00000 3.02600 -2 3.02600 3.02600 0.00000

CdTe 0 1

Cd 0.00000 0.00000 0.00000 Te 1.62000 1.62000 1.62000 -2 0.00000 3.24000 3.24000 -2 3.24000 0.00000 3.24000 -2 3.24000 3.24000 0.00000

GaAs

0 1 Ga 0.00000 0.00000 0.00000

As 1.43150 1.43150 1.43150 -2 0.00000 2.86300 2.86300 -2 2.86300 0.00000 2.86300 -2 2.86300 2.86300 0.00000

GaN

0 1 Ga 0.00000 0.00000 0.00000

N 1.12450 1.12450 1.12450 -2 0.00000 2.24900 2.24900 -2 2.24900 0.00000 2.24900 -2 2.24900 2.24900 0.00000

GaNwu

0 1 Ga 1.58000 0.91220 0.00000

Ga 1.58000 -0.91220 2.56250 N 1.58000 0.91220 1.92190 N 1.58000 -0.91220 4.48440 -2 1.58000 -2.73660 0.00000 -2 1.58000 2.73660 0.00000 -2 0.00000 0.00000 5.12500

S-58

GaP 0 1

Ga 0.00000 0.00000 0.00000 P 1.36380 1.36380 1.36380

-2 0.00000 2.72750 2.72750 -2 2.72750 0.00000 2.72750 -2 2.72750 2.72750 0.00000

GaSb 0 1

Ga 0.00000 0.00000 0.00000 Sb 1.52400 1.52400 1.52400 -2 0.00000 3.04800 3.04800 -2 3.04800 0.00000 3.04800 -2 3.04800 3.04800 0.00000

Ge 0 1

Ge 0.00000 0.00000 0.00000 Ge 1.41250 1.41250 1.41250 -2 0.00000 2.82500 2.82500 -2 2.82500 0.00000 2.82500 -2 2.82500 2.82500 0.00000

InAs 0 1

In 0.00000 0.00000 0.00000 As 1.51450 1.51450 1.51450 -2 0.00000 3.02900 3.02900 -2 3.02900 0.00000 3.02900 -2 3.02900 3.02900 0.00000

InN 0 1

In 1.76850 1.02100 0.00000 In 1.76850 -1.02100 2.85200 N 1.76850 1.02100 2.13900 N 1.76850 -1.02100 4.99100 -2 1.76850 -3.06310 0.00000 -2 1.76850 3.06310 0.00000 -2 0.00000 0.00000 5.70400

S-59

InP 0 1

In 0.00000 0.00000 0.00000 P 1.46720 1.46720 1.46720

-2 0.00000 2.93450 2.93450 -2 2.93450 0.00000 2.93450 -2 2.93450 2.93450 0.00000

InSb 0 1

In 0.00000 0.00000 0.00000 Sb 1.61980 1.61980 1.61980 -2 0.00000 3.23950 3.23950 -2 3.23950 0.00000 3.23950 -2 3.23950 3.23950 0.00000

MgS 0 1

Mg 0.00000 0.00000 0.00000 S 1.40550 1.40550 1.40550

-2 0.00000 2.81100 2.81100 -2 2.81100 0.00000 2.81100 -2 2.81100 2.81100 0.00000

MgSe 0 1

Mg 0.00000 0.00000 0.00000 Se 2.70000 2.70000 2.70000 -2 0.00000 2.70000 2.70000 -2 2.70000 0.00000 2.70000 -2 2.70000 2.70000 0.00000

MgTe 0 1

Mg 0.00000 0.00000 0.00000 Te 1.61130 1.61130 1.61130 -2 0.00000 3.22250 3.22250 -2 3.22250 0.00000 3.22250 -2 3.22250 3.22250 0.00000

SiC 0 1

Si 0.00000 0.00000 0.00000

S-60

C 1.09250 1.09250 1.09250 -2 0.00000 2.18500 2.18500 -2 2.18500 0.00000 2.18500 -2 2.18500 2.18500 0.00000

Si 0 1

Si 0.00000 0.00000 0.00000 Si 1.35750 1.35750 1.35750 -2 0.00000 2.71500 2.71500 -2 2.71500 0.00000 2.71500 -2 2.71500 2.71500 0.00000

ZnO 0 1

Zn -0.82273 0.47197 -2.33109 Zn 0.82071 -0.47267 0.32441 O -0.82068 0.48610 -0.32441 O 0.82270 -0.48540 2.33109 -2 3.29094 -0.01613 -0.00320 -2 -1.631387 2.850389 0.00054 -2 0.005344 0.001885 5.313519

ZnS 0,1 Zn 0.00000 0.00000 0.00000

S 1.35220 1.35220 1.35220 -2 0.00000 2.70450 2.70450 -2 2.70450 0.00000 2.70450 -2 2.70450 2.70450 0.00000

ZnSe 0,1 Zn 0.00000 0.00000 0.00000

Se 1.41700 1.41700 1.41700 -2 0.00000 2.83400 2.83400 -2 2.83400 0.00000 2.83400 -2 2.83400 2.83400 0.00000

ZnTe 0,1 Zn 0.00000 0.00000 0.00000

Te 1.52230 1.52230 1.52230

S-61

-2 0.00000 3.04450 3.04450 -2 3.04450 0.00000 3.04450 -2 3.04450 3.04450 0.00000

S-62

EE69

acetaldehyde 0 1

O 1.212008 0.374458 0.000000 C 0.000000 0.462805 0.000000 H -0.486928 1.460337 0.000000 C -0.941279 -0.711815 0.000000 H -0.384684 -1.649523 0.000000 H -1.588387 -0.656210 0.881703 H -1.588387 -0.656210 -0.881703

acetone 0 1

O 0.000000 0.000000 1.404559 C 0.000000 0.000000 0.184831 C 0.000000 1.286642 -0.616357 C 0.000000 -1.286642 -0.616357 H 0.000000 2.145130 0.055418 H 0.000000 -2.145130 0.055418 H -0.881514 1.320931 -1.265003 H 0.881514 1.320931 -1.265003 H 0.881514 -1.320931 -1.265003 H -0.881514 -1.320931 -1.265003

ethylene 0 1

C 0.000000 0.000000 0.669575 C 0.000000 0.000000 -0.669575 H 0.000000 0.926294 1.235309 H 0.000000 -0.926294 1.235309 H 0.000000 0.926294 -1.235309 H 0.000000 -0.926294 -1.235309

formaldehyde 0 1

C 0.000000 0.000000 -0.533319 O 0.000000 0.000000 0.679545 H 0.000000 0.937366 -1.118221 H 0.000000 -0.937366 -1.118221

S-63

isobutene 0 1

C 0.000000 0.000000 1.463400 C 0.000000 0.000000 0.119614 H 0.000000 0.928447 2.027281 H 0.000000 -0.928447 2.027281 C 0.000000 1.276163 -0.680400 H 0.000000 2.156688 -0.032951 H 0.881626 1.321381 -1.330486 H -0.881626 1.321381 -1.330486 C 0.000000 -1.276163 -0.680400 H 0.000000 -2.156688 -0.032951 H -0.881626 -1.321381 -1.330486 H 0.881626 -1.321381 -1.330486

pyrazine 0 1

C 0.000000 1.133849 0.699678 C 0.000000 1.133849 -0.699678 N 0.000000 0.000000 -1.420331 C 0.000000 -1.133849 -0.699678 C 0.000000 -1.133849 0.699678 N 0.000000 0.000000 1.420331 H 0.000000 2.068862 1.254885 H 0.000000 2.068862 -1.254885 H 0.000000 -2.068862 -1.254885 H 0.000000 -2.068862 1.254885

pyridazine 0 1

N 0.000000 0.670782 -1.238620 C 0.000000 1.325351 -0.064846 C 0.000000 0.694555 1.184924 C 0.000000 -0.694555 1.184924 C 0.000000 -1.325351 -0.064846 N 0.000000 -0.670782 -1.238620 H 0.000000 1.274441 2.102771 H 0.000000 2.408352 -0.152902 H 0.000000 -1.274441 2.102771 H 0.000000 -2.408352 -0.152902

S-64

pyridine 0 1

N 0.000000 0.000000 1.428332 C 0.000000 0.000000 -1.391651 C 0.000000 1.144923 0.723091 C 0.000000 -1.144923 0.723091 C 0.000000 -1.199476 -0.674912 C 0.000000 1.199476 -0.674912 H 0.000000 0.000000 -2.478143 H 0.000000 2.061946 1.308643 H 0.000000 -2.061946 1.308643 H 0.000000 -2.159346 -1.182856 H 0.000000 2.159346 -1.182856

pyrimidine 0 1

C 0.000000 0.000000 -1.312458 N 0.000000 1.203128 -0.717845 C 0.000000 1.188178 0.625296 C 0.000000 0.000000 1.356430 C 0.000000 -1.188178 0.625296 N 0.000000 -1.203128 -0.717845 H 0.000000 2.156668 1.120301 H 0.000000 0.000000 -2.399286 H 0.000000 0.000000 2.441125 H 0.000000 -2.156668 1.120301

stetrazine 0 1

C 0.000000 0.000000 1.265707 N 0.000000 1.203065 -0.667089 C 0.000000 0.000000 -1.265707 N 0.000000 -1.203065 0.667089 H 0.000000 0.000000 2.350926 H 0.000000 0.000000 -2.350926 N 0.000000 -1.203065 -0.667089 N 0.000000 1.203065 0.667089

tbutadiene 0 1

C 0.608308 1.751027 0.000000 C 0.608308 0.403889 0.000000 C -0.608308 -0.403889 0.000000

S-65

C -0.608308 -1.751027 0.000000 H 1.533770 2.317122 0.000000 H -0.322818 2.311810 0.000000 H 1.556392 -0.133780 0.000000 H -1.556392 0.133780 0.000000 H 0.322818 -2.311810 0.000000 H -1.533770 -2.317122 0.000000

S-66

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MN15: A New Kohn-Sham Density Functional with Broad ... · 0 2006 b97-d 21 0 2009 mohlyp2 22 0 2009 orelyp 10,18,23 nga nga 0 2012 n12 24 0 2015 gam 25 meta-gga mgga 0 1998 vsxc 26